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[ CAS No. 902518-11-0 ] {[proInfo.proName]}

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Chemical Structure| 902518-11-0
Chemical Structure| 902518-11-0
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Quality Control of [ 902518-11-0 ]

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Product Details of [ 902518-11-0 ]

CAS No. :902518-11-0 MDL No. :MFCD23135883
Formula : C18H12BrN Boiling Point : -
Linear Structure Formula :- InChI Key :KEWDVYIULXXMPP-UHFFFAOYSA-N
M.W : 322.20 Pubchem ID :59465012
Synonyms :

Calculated chemistry of [ 902518-11-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 19
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 88.48
TPSA : 4.93 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.16
Log Po/w (XLOGP3) : 5.69
Log Po/w (WLOGP) : 5.55
Log Po/w (MLOGP) : 5.01
Log Po/w (SILICOS-IT) : 4.74
Consensus Log Po/w : 4.83

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.06
Solubility : 0.000281 mg/ml ; 0.000000872 mol/l
Class : Poorly soluble
Log S (Ali) : -5.56
Solubility : 0.000889 mg/ml ; 0.00000276 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.48
Solubility : 0.0000107 mg/ml ; 0.0000000331 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 902518-11-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 902518-11-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 902518-11-0 ]

[ 902518-11-0 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 583-55-1 ]
  • [ 86-74-8 ]
  • [ 902518-11-0 ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; for 12h;Inert atmosphere; Reflux; 20 g (119.61 mmol) of carbazole, 67.68 g (239.22 mmol) of 2-bromoidobenzene, 11.40 g (59.81 mmol) of copper iodide, and 33.06 g (239.22 mmol) of potassium carbonate were dissolved in xylene in a nitrogen atmosphere, and the mixture was refluxed while stirring. After 12 hours, the mixture was cooled to room temperature, distilled water was added thereto, and the mixture was subjected to extraction using methyl chloride (MC), dried using magnesium sulfate, and distilled under reduced pressure. The resultant was separation-purified using column chromatography to obtain 32.64 g (101.67 mmol, 85% yield) of Intermediate 1-1.
56% With copper(l) iodide; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; for 48h;Inert atmosphere; Reflux; (1) In the reaction flask carbazole 3.0g, o-bromo-iodobenzene 10.15g, 2.39 g copper iodide, 4.95g of potassium carbonate and 40mL of dry xylene, the reaction was refluxed for 48 hours nitrogen, was added 50mL of water quench off the reaction, extracted with dichloromethane, the solvent was evaporated, purified by column chromatography, a white precipitate was finally obtained 9- (2-bromophenyl) -9H- carbazole 2.5g, 56% yield.
47% With copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 48h; Carbazole (1 eq) and o-bromoiodobenzene (3 eq) cuprous iodide (0.05 eq); 11 g potassium carbonate (4 eq) was added to a three-neck bottle.Add anhydrous N,N-dimethylformamide (DMF) and react at 140 C for 48 h.After the reaction was completed, the reaction system was poured into water to precipitate a large amount of solid, and the solid was dissolved in dichloromethane, and the mixture was applied to a white solid (47%);
29% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 100℃; for 20h;Inert atmosphere; Reflux; Sigma aldrich in nitrogen (http://www. Sigmaaldrich. Com /) carbazole yarn (50 g, 299. 0 mmol) of toluene 0. 5 L senses a rotation velocity of the disk to, herein 1-bromo-2-iodobenzene sigma aldrich yarn (101. 5 g, 358. 8 mmol), bis (dibenzylideneacetone) palladium (0) (5. 16 g, 8. 97 mmol), tris-tert butylphosphine (3. 02 g, 15. 0 mmol) and sodium tert-butoxide (34. 5 g, 358. 8 mmol) in 100 C sequentially and at the reflux by heating at a 20. Complete after reaction solution at a water doesn't have any error frames, then dichloromethane (DCM) extraction of water to the MgSO4 anhydride after triggers number, filter and was, concentrating it under reduced pressure. Thus-obtained residue number intermediate that is forward separated into flash column chromatography I-3 (27. 9 g, 29%) a obtained.
25% With potassium carbonate;copper(l) iodide; In xylene;Heating / reflux; Carbazole (1.672 g, 10 mmol), l-bromo-2-iodobenzene (1.5 ml, 12 mmol), potassium carbonate (K CO , 2.7646 g, 20 mmol), copper iodide (CuI, 95 mg, 0.5 mmol), and 25 ml of xylene were refluxed in a nitrogen atmosphere. After cooling to normal temperature was conducted, a product was extracted with ethyl acetate, water was removed with anhydrous magnesium sulfate (MgSO ), and the solvent was removed at a reduced pressure. The resulting product was passed through a silica gel column using a hexane solvent to produce a compound, the solvent was removed at a reduced pressure, and vacuum drying was conducted to produce the resulting white solid compound of Formula a (800 mg, yield 25%).[123] MS: [M+H]+ = 323.
25% With potassium carbonate;copper(l) iodide; In xylene;Reflux; Inert atmosphere; Preparation Example 1Preparation of Starting Material Represented by Formula aCarbazole (1.672 g, 10 mmol), 1-bromo-2-iodobenzene (1.5 ml, 12 mmol), potassium carbonate (K2CO3, 2.7646 g, 20 mmol), copper iodide (Cud, 95 mg, 0.5 mmol), and 25 ml of xylene were refluxed in a nitrogen atmosphere. After cooling to normal temperature was conducted, a product was extracted with ethyl acetate, water was removed with anhydrous magnesium sulfate (MgSO4), and the solvent was removed at a reduced pressure. The resulting product was passed through a silica gel column using a hexane solvent to produce a compound, the solvent was removed at a reduced pressure, and vacuum drying was conducted to produce the resulting white solid compound of Formula a (800 mg, yield 25%).MS: [M+H]+=323.
25% With potassium carbonate;copper(l) iodide; In xylene;Reflux; Inert atmosphere; Preparation Example 1Preparation of Starting Material Represented by Formula aCarbazole (1.672 g, 10 mmol), 1-bromo-2-iodobenzene (1.5 ml, 12 mmol), potassium carbonate (K2CO3.2.7646 g, 20 mmol), copper iodide (CuI, 95 mg, 0.5 mmol), and 25 ml of xylene were refluxed in a nitrogen atmosphere. After cooling to normal temperature was conducted, a product was extracted with ethyl acetate, water was removed with anhydrous magnesium sulfate (MgSO4), and the solvent was removed at a reduced pressure. The resulting product was passed through a silica gel column using a hexane solvent to produce a compound, the solvent was removed at a reduced pressure, and vacuum drying was conducted to produce the desired white solid compound (800 mg, yield 25%).MS: [M+H]+=323.
25% With copper(l) iodide; potassium carbonate; In N,N-dimethyl acetamide; at 130℃; for 48h;Inert atmosphere; General procedure: A mixture of carbazole(1.67 g, 10 mmol), 2-bromoiodobenzene (4.2 g, 15 mmol), K2CO3 (2.76 g, 20 mmol), CuI (0.95 g, 5 mmol) and DMA (100 mL) in a 250 mL three-necked flask was heated at 130 C for 48 h under nitrogen. After cooling, it was poured into water (200 mL) and extracted with CH2Cl2, the combined organic phase was washed with water and dried over MgSO4. After workup, the crude product was isolated by column chromatography (PE) to afford white powder (1.5 g, 25 %); Rf = 0.26 (PE); M. p.: 110 - 112 C; 1H NMR (CDCl3, 500 MHz) delta: 8.17(d, J = 7.7 Hz, 2H), 7.88 (d, J = 8.0 Hz, 1H), 7.52 (m, 2H), 7.43 (m, 3H), 7.31 (t, J = 7.33 Hz, 2H), 7.08 (d, J = 8.1 Hz, 2H); 13C NMR (CDCl3, 125 MHz) delta: 140.84, 136.77, 134.23, 131.13, 130.14, 128.80, 125.92, 123.85, 123.25, 120.33, 119.98, 110.01.
25.5% With copper(l) iodide; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; at 120℃; Carbazole (7.39 g, 0.0442 mol), 1-bromo-2-iodobenzene (25 g, 0.0883 mol), CuI (0.421 g, 2.22 mmol), K2CO3 (12.12 g, 0.0883 mol) in a 500 mL 2-neck flask Mol) were dissolved in xylene and refluxed and stirred at 120 C. The mixture was cooled to room temperature, extracted with CH2Cl2, dried over MgSO4, and then the solvent was removed. Hexane solvent to obtain 3.63 g (25.5%) of a white solid.
25% With copper(l) iodide; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene;Inert atmosphere; Reflux; Under nitrogen atmosphere, a mixture of carbazole (1.7 g), 1-bromo-2-iodobenzene (1.5 ml), potassium carbonate (2.8 g), copper iodide (95 mg), and xylene (25 ml) was refluxed. After cooling to ordinary temperature, the reaction product was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then, the solvent was removed under reduced pressure. The residue was passed through a silica gel column by using a hexane solvent, and then, the solvent was removed under reduced pressure. The obtained residue was vacuum-dried to obtain the intermediate a as a white solid (800 mg, 25% yield). MS: [M+H]+=323
25% With copper(l) iodide; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene;Inert atmosphere; Reflux; Under nitrogen atmosphere, a mixture of carbazole (1.7 g), 1-bromo-2-iodobenzene (1.5 ml), potassium carbonate (2.8 g), copper iodide (95 mg), and xylene (25 ml) was refluxed. After cooling to ordinary temperature, the reaction product was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then, the solvent was removed under reduced pressure. The residue was passed through a silica gel column by using a hexane solvent, and then, the solvent was removed under reduced pressure. The obtained residue was vacuum-dried to obtain the intermediate a as a white solid (800 mg, 25% yield). MS: [M+H]+=323
25% With copper(l) iodide; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene;Reflux; Inert atmosphere; Carbazole (1.7 g),1-bromo-2-iodobenzene (1.5 ml),Potassium carbonate (2.8 g),Copper iodide (95 mg) and xylene (25 ml) were refluxed under an atmosphere of nitrogen.After cooling to normal temperature, the product was extracted with ethyl acetate.After drying the extract with anhydrous magnesium sulfate,The solvent was removed under reduced pressure.Passed through a silica gel column using a hexane solvent, the solvent was removed under reduced pressure,The obtained residue was dried under vacuum to obtain an intermediate a (800 mg, 25% yield) as a white solid.
With copper(l) iodide; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene;Reflux; Inert atmosphere; 1.672 g of carbazole, 1.6 mL of 1-bromo-2-iodobenzene, 2.7646 g potassium carbonate, 95 mg of copper iodide, and 25 mL of xylene were refluxed in a nitrogen atmosphere. The mixture was cooled to room temperature, extracted with ethyl acetate, and dried with anhydrous magnesium sulfate to remove moisture, and the solvent was removed under reduced pressure. Silica gel column separation using a hexane solvent was conducted, thus obtaining a compound from which the solvent was then removed under reduced pressure, followed by vacuum drying, yielding 9-(2-bromophenyl)-9H-carbazole as a desired white solid intermediate.

  • 2
  • [ 902518-11-0 ]
  • [ 3988-03-2 ]
  • C31H20Br3N [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.4% The starting material represented by Formula a (6.96 g, 21.6 mmol) was dissolved in 300 ml of purified THF (tetrahydrofuran) and cooled to -780C, and n-BuLi (2.5 M in hexane, 8.64 ml, 21.6 mmol) was slowly dropped thereon. Stirring was conducted at the same temperature for 30 min, and 4,4'-dibromobenzophenone (6.12 g, 18.0 mmol) was added thereto. After stirring was conducted at the same temperature for 40 min, the temperature was raised to normal temperature and stirring was carried out for an additional 3 hours. The reaction was completed in an ammonium chloride (NH Cl) aqueous solution, and extraction was conducted with ethyl ether. Water was removed from an organic material layer using anhydrous magnesium sulfate (MgSO ), and an organic solvent was then removed therefrom. The produced solid was dispersed in ethanol, stirred for one day, filtered, and vacuum dried to produce 10.12 g of intermediate material (96.4percent yield).
  • 3
  • [ 902518-11-0 ]
  • [ 3988-03-2 ]
  • C32H23Br2NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.4% Preparation Example 2Preparation of Starting Material Represented by Formula bThe starting material represented by Formula a (6.96 g, 21.6 mmol) was dissolved in 300 ml of purified THF (tetrahydrofuran) and cooled to -78° C., and n-BuLi (2.5 M in hexane, 8.64 ml, 21.6 mmol) was slowly dropped thereon. Stirring was conducted at the same temperature for 30 min, and 4,4'-dibromobenzophenone (6.12 g, 18.0 mmol) was added thereto. After stirring was conducted at the same temperature for 40 min, the temperature was raised to normal temperature and stirring was carried out for an additional 3 hours. The reaction was completed in an ammonium chloride (NH4Cl) aqueous solution, and extraction was conducted with ethyl ether. Water was removed from an organic material layer using anhydrous magnesium sulfate (MgSO4), and an organic solvent was then removed therefrom. The produced solid was dispersed in ethanol, stirred for one day, filtered, and vacuum dried to produce 10.12 g of intermediate material (96.4percent yield). The intermediate solid was dispersed in 10 ml of acetic acid, ten drops of concentrated sulfuric acid were added thereto, and reflux was conducted for 4 hours. The resulting solid was filtered, washed with ethanol, and vacuum dried to produce 9.49 g of compound of Formula b (yield 96.8percent).MS: [M+H]+=565.
  • 4
  • [ 119-61-9 ]
  • [ 902518-11-0 ]
  • [ 1246199-75-6 ]
  • 5
  • [ 902518-11-0 ]
  • [ 90-90-4 ]
  • [ 1029613-69-1 ]
YieldReaction ConditionsOperation in experiment
1.0 g of <strong>[902518-11-0]9-(2-bromophenyl)-9H-carbazole</strong> as the intermediate of preparation example 8 was dissolved in 10 mL of purified tetrahydrofuran, and the resulting solution was cooled to -78 degree C, and 1.613 mL of butyllithium was slowly added dropwise. The mixture was stirred at the same temperature for 30 min, and 1.05 g of 4-bromobenzophenone was added. The mixture was stirred at the same temperature for 40 minutes, and then further stirred at room temperature for an additional 3 hours. The reaction was terminated with aqueous ammonium chloride, and the reaction mixture was extracted with ethyl ether. The organic layer was dewatered using anhydrous magnesium sulfate, and the organic solvent was then removed. The resulting solid was then dispersed in ethanol, stirred for one day, filtered and vacuum dried, thus obtaining an intermediate material. The solid thus obtained was dispersed in 10 ml of acetic acid, and 10 drops of concentrated sulfuric acid were added, after which the mixture was refluxed for 4 hours. The resulting solid was filtered, washed with ethanol, and vacuum dried, yielding 8-(4-bromophenyl)-8-phenyl-8H-indolo-[3,2,1-de]acridine compound.
  • 6
  • [ 902518-11-0 ]
  • [ 3988-03-2 ]
  • [ 1029634-23-8 ]
YieldReaction ConditionsOperation in experiment
6.96 g of <strong>[902518-11-0]9-(2-bromophenyl)-9H-carbazole</strong> as the intermediate Preparation example 8 was dissolved in 10 mL of purified tetrahydrofuran, and the resulting solution was cooled to -78 degree C, and 8.64 mL of butyllithium was slowly added dropwise. The mixture was stirred at the same temperature for 30 minutes, and 6.12 g of 4,4'-dibromobenzophenone was added. The mixture was stirred for 40 minutes at the same temperature, and then further stirred at room temperature for additional 3 hours. The reaction was terminated with aqueous ammonium chloride, and the reacrtion mixture was extracted with ethyl ether. The organic solvent was dewatered using anhydrous magnesium sulfate, and the organic solvent was then removed. The resulting solid was dispersed in ethanol, stirred for one day, filtered, and vacuum dried, thus obtaining an intermediate material. The solid thus obtained was dispersed in 10 mL of acetic acid, and 10 drops of concentrated sulfuric acid were added, after which the mixture was refluxed for 4 hours. The resulting solid was filtered, washed with ethanol, and vacuum dried, yielding 8,8 -bis (4-bromophenyl)-8H-indolo [3,2,1-de] acridine compound.
  • 7
  • [ 686-69-1 ]
  • [ 902518-11-0 ]
  • [ 1308652-66-5 ]
  • 8
  • [ 902518-11-0 ]
  • [ 13716-10-4 ]
  • [ 1262046-40-1 ]
  • 9
  • [ 902518-11-0 ]
  • [ 40244-90-4 ]
  • [ 1308652-65-4 ]
  • 11
  • [ 902518-11-0 ]
  • [ 16523-54-9 ]
  • [ 1308652-64-3 ]
YieldReaction ConditionsOperation in experiment
88.3% (Setting-Up and Reaction) To a 200 mL four-necked round-bottomed flask, a three-way stopcock, a Teflon-coated magnetic stirring bar, a 20 mL dropping funnel, and a thermometer were attached, and the inside was purged with nitrogen. To this flask, <strong>[902518-11-0]N-(2-bromophenyl)carbazole</strong> (7) (8.8 g, 27.3 mmol, 1.0 eq.) obtained in the first step and anhydrous tetrahydrofuran (hereinafter, abbreviated as THF) (54.6 mL) were sequentially added, and the obtained reactant solution was cooled to -70C by use of a dry ice/acetone bath. Subsequently, a n-butyllithium (hereinafter, abbreviated as n-BuLi)/n-hexane solution (1.60 mol/L, 17. 9 mL, 28. 6 mmol, 1.05 eq.) was placed in the dropping funnel, and added dropwise over 15 minutes, while the reactant solution was being stirred, and the inside temperature was being kept at -50C or below. Then, the dropping funnel was rinsed with anhydrous n-hexane (1 mL) . The obtained cream-colored suspension was stirred at -70C for 1 hour. Then, an anhydrous THF (14 mL) solution of chlorodicyclohexylphosphine (hereinafter, abbreviated as Cy2PCl) (7.0 g, 30.1 mmol, 1.1 eq.) was placed in the dropping funnel, and added dropwise over 15 minutes, while the suspension was being stirred, and the inside temperature was being kept at -50 C or below (the suspension was dissolved rapidly). After completion of the dropwise addition, the dry ice/acetone bath was taken out, and the temperature of the reaction solution was raised to room temperature over 30 minutes, followed by stirring for further 30 minutes. (Post Treatment and Purification) After the reaction solution had been concentrated under reduced pressure, toluene and an aqueous solution of sodium hydrogen carbonate (2.3 g, approximately 1 eq.) were added to the residue. The mixture was transferred to a separating funnel, shaken and allowed to stand, and the layers were separated (Aqueous Layer 1: pH=9). Then, the organic layer was further washed with water (Aqueous Layer 2: pH=7). The solvent was distilled off from the organic layer under reduced pressure, and toluene and silica gel (0.7 g) were added to the obtained light brown residue. The mixture was stirred at room temperature for 10 minutes and filtered by use of diatomaceous earth, and the residue was washed with toluene. The filtrate was concentrated, until crystals were precipitated. Then, methanol was added, and the obtained white suspension was filtered. The product obtained by the filtration was washed with methanol, and then dried under reduced pressure to give 10.6 g of title compound (2-1) as a colorless powder. Isolated Yield: 88.3%. 1H NMR (300 MHz, CDCl3): delta=8.12 (d, J=7.5 Hz, 2H), 7.76 (dt, J=1.5, 4.8 Hz, 1H), 7.57-7.47 (m, 2H), 7.38-7.28 (m, 3H), 7.23 (dt, J=0.9, 6.9 Hz, 2H), 7.02 (d, J=8.1 Hz, 2H), 1.85-1.38 (m, 12H), 1.22-0.90 (m, 10H). 31P NMR (121 MHz, CDCl3): delta=-14.5.
  • 12
  • [ 86-74-8 ]
  • [ 583-53-9 ]
  • [ 902518-11-0 ]
YieldReaction ConditionsOperation in experiment
83% (1) The carbazole 8.36g (0.05mol), o-dibromobenzene 17.69g (0.075mol), potassium carbonate 17.97g (0.13mol) placed in the reactor, stirred, purged with nitrogen for 30min,1.91 g of cuprous iodide and 1.46 g of L-lysine were added and heated to 163 ° C. for 38 h.No raw material was detected by TLC, and a large amount of water was added to terminate the reaction. The solid was precipitated by stirring and dried under suction filtration to give 13.37 g of 9- (2-bromophenyl) carbazole as solid, yield 83percent.
55% With copper(I) oxide; potassium phosphate; N,N`-dimethylethylenediamine; In toluene; at 120℃; for 72h; 9-Carbazole (6.52 g, 39 mmol), 1,2-dibromobenzene (8 mL,66.3 mmol), copper(I) oxide (1.116 g, 7.8 mmol), N,N'-dimethylethylenediamine (1.70 mL, 15.6 mmol) and anhydrous potassium phosphate (18.21 g, 85.8 mmol) were mixed in 50 mL of anhydrous toluene and heated at 120 °C for 3 days. The crude reaction mixture was extracted with dichloromethane and water. The organic layerwas dried with anhydrous MgSO4, filtered, and evaporated. The crude product was purified by column chromatography on silica gelusing 1:30 dichloromethane/hexane. The white powder wasformed. (6.95 g, Yield 55percent) 1H NMR (300 MHz, CDCl3): delta (ppm)8.14-8.17 (d, 2H), 7.85-7.88 (d, 1H), 7.47-7.57 (m, 2H), 7.37-7.45(m, 3H), 7.27-7.32 (m, 2H), 7.05-7.08 (d, 2H).
55% With copper; potassium carbonate; In dimethyl sulfoxide; at 20℃; for 20.5h;Inert atmosphere; Reflux; A 500-mL, three-necked round bottom flask was charged with 9.7 g (0.058 mol) of the compound carbazole in a nitrogen atmosphere and diluted with 200 mL of dimethylsulfoxide. 15 g of 1,2-dibromobenzene, 3.7 g of copper powder and 12 g of potassium carbonate were added to the diluted solution, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was heated and refluxed for 20 hours. The reaction solution was cooled to room temperature and extracted with dichloromethane and distilled water. The extract was dried and concentrated under reduced pressure to obtain 10.3 g (yield: 55percent) of Compound 11-1.
53% With copper(l) iodide; 18-crown-6 ether; In 1,2-dichloro-benzene; at 100 - 210℃;Inert atmosphere; Darkness; Carbazole (1.6700 g, 10.0 mmol), o-dibromobenzene (2.40 mL, 20.0 mmol),Copper iodide (0.1900 g, 1.0 mmol), 18-crown-6 (0.1320 g, 0.5 mmol), 60mL o-dichlorobenzene was added to the reaction flask in turn, under nitrogen protection and dark conditions,Stir heated to 100-210°C, react for 5-100 hours, stop the reaction and slowly reduce to room temperature, Most of the solvent was distilled off under reduced pressure. The solid residue was suction filtered and washed with dichloromethane solution. The organic phase was combined. Concentration and column chromatography gave N-(2-bromophenyl)carbazole; (yield: 53percent)
39% With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide; In o-xylene; for 8h;Reflux; Inert atmosphere; In a one-neck flask, carbazole (3.3g, 19.9mmol), o-dibromobenzene (4.5g, 19.9mmol), CuI (0.8g, 4.0mmol), 1,10-phenanthroline monohydrate (0.8g, 4.0mmol) and KOH (2.3g, 40mmol)were dissolved in o-x1ylene (50mL). The mixture was heated to reflux for 8h under nitrogen. After the reaction had all reacted, the mixture was allowed to cool to room temperature and then CH2Cl2 (50mL) was poured into the mixture. The organic layer was dried over anhydrous MgSO4 and concentrated this by a rotary evaporator. The crude materials were purified by silica gel column chromatography (petroleum ether/CH2Cl2=4: 1 v/v) to obtain a white solid 1.5g, 39percent. 1H NMR (400MHz, DMSO-d6, TMS) delta: 8.25 (d, J=7.6Hz, 2H), 8.00 (dd, J=8.0, 1.2Hz, 1H), 7.68 (m, 2H), 7.62?7.56 (m, 1H), 7.45?7.38 (m, 2H), 7.32?7.25 (m, 2H), 7.00 (d, J=8.0H, 2H). 13C NMR (126MHz, CDCl3) delta: 140.84, 140.49, 134.25, 131.16, 130.64, 130.17, 129.78, 128.83, 125.94, 123.24, 120.36, 119.99, 110.14, 110.03. HRMS (m/z): [M+H]? calcd for C18H12BrN, 322.0231; found, 322.0250.
With copper(l) iodide; potassium carbonate; In N,N-dimethyl acetamide; for 24h;Inert atmosphere; Reflux; A mixture of 9H-carbazole (5.5 g, 32.89 mmol), 1,2-dibromobenzene (11.64 g, 49.34 mmol), cupper iodide (3.13 g,16.45 mmol), and potassium carbonate (9.09 g, 65.79 mmol) inanhydrous N,N-dimethylacetamide (120 mL) was degassed withnitrogen for 30 min while stirring. The reaction mixture was thenrefluxed under a nitrogen atmosphere for 24 h. The crude mixturewas filtered, and the residue was washed thrice with dichloromethane(50 mL). The combined filtrates were evaporated to dryness.The residue was purified through column chromatography(silica gel, 50percent n-hexane in dichloromethane) to yield 9-(2-bromophenyl)-9H-carbazole as a white solid.1H NMR (500 MHz, CDCl3): d 7.06 (d, 2H, J 12 Hz), 7.28 (t, 2H,J 18 Hz), 7.39 (t, 3H, J 18 Hz), 7.43e7.52 (m, 2H), 7.84 (d, 1H,J 12 Hz), 8.14 (d, 2H, J 12 Hz).
With copper(l) iodide; potassium carbonate; In N,N-dimethyl acetamide; for 24h;Inert atmosphere; Reflux; A mixture of 9H-carbazole (5.5 g, 32.89 mmol), 1,2-dibromobenzene (11.64 g, 49.34 mmol), copper iodide (3.13 g,16.45 mmol), and potassium carbonate (9.09 g, 65.79 mmol) inanhydrous N,N-dimethylacetamide (120 mL) was degassed withnitrogen for 30 min while stirring. The reaction mixture was thenrefluxed in nitrogen for 24 h. The crude mixture was filtered, andthe residue was washed with dichloromethane (3 x 50 mL). Thecombined filtrates were evaporated until they were dry The residue was purified by column chromatography (silica gel, 50percent n-hexanein dichloromethane) to give 9-(2-bromophenyl)-9H-carbazole as awhite solid.1H NMR (500 MHz, CDCl3): delta 7.06 (d, 2H, J = 12 Hz), 7.28 (t, 2H,J = 18 Hz), 7.39 (t, 3H, J = 18 Hz), 7.43-7.52 (m, 2H), 7.84 (d, 1H,J = 12 Hz), 8.14 (d, 2H, J = 12 Hz). 13C NMR (CDCl3): delta 110.0, 120.0,120.3, 123.2, 123.8, 125.9, 128.8, 130.1, 131.1, 134.2, 136.7, 140.8.

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