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[ CAS No. 19591-17-4 ] {[proInfo.proName]}

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Chemical Structure| 19591-17-4
Chemical Structure| 19591-17-4
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CAS No. :19591-17-4 MDL No. :MFCD00099251
Formula : C8H8INO Boiling Point : -
Linear Structure Formula :- InChI Key :BCJOKHQYEDXBSF-UHFFFAOYSA-N
M.W : 261.06 Pubchem ID :140559
Synonyms :

Safety of [ 19591-17-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19591-17-4 ]

* 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 [ 19591-17-4 ]

[ 19591-17-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 615-43-0 ]
  • [ 108-24-7 ]
  • [ 19591-17-4 ]
YieldReaction ConditionsOperation in experiment
85% With sulfuric acid; at 20℃; for 0.0833333h; One drop of concentrated H2SO4 was added to a stirred solution of 2-iodoaniline (100 mg; 0.46 mmol) in acetic anhydride (100 mL). The resulting mixture was stirred at room temperature for 5 min and then quenched with water and extracted with ethyl acetate (3 x 5 mL). The combined organic layers were washed with water, brine and dried with anhydrous sodium sulfate. The solvent was removed and the crude product was crystallized from ethanol to give the N-acetyl derivative as a crystalline solid in 85% yield, mp:102-104 C.
75% With triethylamine; In dichloromethane; at 0 - 20℃; for 19h;Inert atmosphere; 2-Iodoaniline (2.2 g, 10.1 mmol, 1.0 equiv) and triethylamine (3.1 mL, 22.2 mmol, 2.2 equiv) weredissolved in CH2Cl2 (25 mL) under argon atmosphere at rt, followed by dropwise addition of aceticanhydride (1.2 mL, 12.1 mmol, 1.2 equiv) at 0 C. The mixture stirred over night at roomtemperature to completion after 19 h, as judged by TLC. The reaction was quenched with water andextracted with CH2Cl2. The combined organic phases were washed with saturated solutions ofsodium bicarbonate and ammonium chloride, dried over anhydrous magnesium sulfate andconcentrated under vacuum. The crude product was purified by column chromatography (pentane:EtOAc 4:1) to give amide 8 (1.987 g, 7.61 mmol, 75%) as colorless crystals.
58% With triethylamine; at 20℃; for 16h;Inert atmosphere; A mixture of 2-iodoaniline (2.2 g, 10.0 mmol), Ac2O (1.2 g, 12.0 mmol) and Et3N (2.2 g, 22 mmol) in DCM was degassed with nitrogen, the mixture was stirred for 16 hours at r.t. The reaction was concentrated in vacuo. The residue was purified by column chromatography to give N-(2-iodophenyl)acetamide (1.6 g, 58% yield) as a white solid. LC/MS (ESI, m/z): [M+1]+=262.1.
With glacial acetic acid; zinc powder; at 20 - 80℃; for 3.5h; 2-Iodoanilines 21,24,25 (2. 2 g, 0.01 mole) were added separately to the mixture of aceticacid (5 mL, 0.08 mole) and acetic anhydride (1.02 g, 0.01 mole) in presence of smallamount of zinc dust and stirred at room temperature for half an hour. The reactionmixture was refluxed for 3 hours with constant stirring at 80 C. The hot reaction mixturewas poured into a beaker containing 200 mL of cold water with constant stirring andextracted with chloroform (3x50 mL). The combined organic layer was washed withdistilled water, dried over anhyd. Na2SO4 and concentrated under reduced pressure. Thecrude product was purified by chromatography on a column of silica gel andcrystallization from ethanol to afford desired products 1-3 in good yield.

  • 2
  • [ 673-32-5 ]
  • [ 19591-17-4 ]
  • [ 78388-92-8 ]
  • 3
  • [ 1942-45-6 ]
  • [ 19591-17-4 ]
  • [ 135189-93-4 ]
  • 5
  • [ 22121-86-4 ]
  • [ 19591-17-4 ]
  • [ 116922-15-7 ]
  • 6
  • [ 39491-65-1 ]
  • [ 19591-17-4 ]
  • [ 127230-09-5 ]
  • 7
  • [ 19591-17-4 ]
  • [ 120789-51-7 ]
  • 1-[2-(tert-Butyl-dimethyl-silanyl)-3-hydroxymethyl-indol-1-yl]-ethanone [ No CAS ]
  • 8
  • [ 19591-17-4 ]
  • [ 148493-34-9 ]
  • [ 148493-40-7 ]
YieldReaction ConditionsOperation in experiment
69% With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere; A mixture of N-(2-iodophenyl)acetamide (261 mg, 1.0 mmol), <strong>[148493-34-9](2,6-dichloropyridin-3-yl)boronic acid</strong> (230 mg, 1.2 mmol), palladium acetate (11 mg, 0.05 mmol), PPh3 (26 mg, 0.1 mmol) and Et3N (303 mg, 3.0 mmol) in DMF was degassed with nitrogen, heated to 100 C. and stirred for 16 hours. The mixture was cooled to r.t, diluted with water and extracted with EA. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give N-(2-(2,6-dichloropyridin-3-yl)phenyl)acetamide (180 mg, 69% yield) as a white solid. LC/MS (ESI, m/z): [M+1]+=282.1
68% With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃; for 6h;Inert atmosphere; Step 1: Synthesis of N-[2-(2,6-dichloro-3-pyridinyl)phenyl]acetamide First, 18.94 g of 2-iodophenylacetamide, 20.73 g of <strong>[148493-34-9]2,6-dichloropyridin-3-boronic acid</strong>, 1.18 g of triphenylphosphine, 0.49 g of palladium acetate, 30 mL of triethylamine, and 290 mL of dry DMF were put into a three-neck flask equipped with a reflux pipe, and the air in the flask was replaced with nitrogen. After that, stirring was performed at 100 C. for 6 hours. Water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The obtained organic layer was washed with saturated saline and dried with magnesium sulfate, and then purified by silica gel column chromatography using hexane and ethyl acetate as a developing solvent in a ratio of 2:1 to give an objective substance as yellow-white powder in a yield of 68%. A synthesis scheme of Step 1 is shown in (a-1).
  • 9
  • [ 19591-17-4 ]
  • [ 107-19-7 ]
  • N-(2-(3-hydroxyprop-1-yn-1-yl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
> 99% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile; at 20℃;Inert atmosphere; General procedure: <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> (100.0 mg, 0.38 mmol, 1.0 equiv) in CH3CN (5.0 mL) was added sequentially with PdCl2(PPh3)2 (5.4 mg, 0.01 mmol, 0.02 equiv), Ph3P (4.0 mg, 0.02 mmol, 0.04equiv), 1-chloro-4-ethynylbenzene (57.6 mg, 0.42 mmol, 1.1 equiv). The resulting solution was degassed by passing through a steady stream of argon for 30 min (flask 1). In the meantime in another flask, a mixture of CuI (3.0 mg, 0.02 mmol, 0.04 equiv) in Et3N was also degassed bypassing through a steady stream of argon for 30 min (flask 2). After degassing, the mixture ofCuI in Et3N in flask 2 was transferred into the solution in flask 1 using a syringe with wide-boarneedle which resulted in the reaction solution turning yellow and giving white precipitates. The reaction mixture was allowed to stir at room temperature overnight and was quenched byaddition with sat. aq. NH4Cl. The separated aqueous phase was extracted with EtOAc (3x times).The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30-50% EtOAc-hexane to yield 114.6 mg of compound 1d (>99%)as a white solid.
92% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 20℃;Inert atmosphere; General procedure: In a round-bottomed flask (50 mL) equipped with <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> [3] (0.8 g, 3.06 mmol), Pd(PPh3)2Cl2 (0.05 g, 0.08 mmol), CuI (0.03 g, 0.15 mmol) and acetonitrile (20 mL), was added 2-methyl-3-butyne-2-ol (0.33 mL, 3.37 mmol) and Et3N (1.71 mL, 12.25 mmol). The mixture was stirred at room temperature for 6-8 h. Upon completion of the reaction (TLC), the mixture was filtered, the solid residue washed with EtOAc and washings added to the filtrate. The combined solution was concentrated under reduced pressure. The oily material obtained was subjected to column chromatography (hexane/ethyl acetate 4:1) to afford the desired product 1a. Propargyl alcohols 1b-1m were prepared by using the same experimental procedure. Among these compounds, 1a and 1d are known.
  • 10
  • [ 615-43-0 ]
  • [ 75-36-5 ]
  • [ 19591-17-4 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine; In dichloromethane; at 0 - 20℃; A solution of 2-iodoaniline (333.6 mg, 1.52 mmol, 1.0 equiv) in DCM (5.0 mL) was added with Et3N (0.23 mL, 166.9 mg, 1.65 mmol, 1.1 equiv). The reaction solution was cooled at 0 C and acetyl chloride (0.28 mL, 308 mg, 3.92 mmol, 2.6 equiv) was added into the cooled solution. The resulting mixture was warmed to stir at room temperature overnight. Upon completion, thereaction was added with water and the separated aqueous phase was extracted with EtOAc (3xtimes). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30% EtOAc-hexane to yield 387.9 mg (98%) of the corresponding N-(2-iodophenyl)acetamide as a white solid.
83% With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 6h; General procedure: Acyl chloride (1.5 equiv) in 5 mL of dry THF was added drop- wise to a stirred, cooled (0-5 C) solution of 2-iodoaniline ( 3 ) (1.0 equiv) and Et 3 N (1.5 equiv) in 20 mL of dry THF. The ice bath was then removed, and the mixture stirred vigorously for 6 hours at room temperature. Solid Et 3 N.HCl was then filtered off, and the fil- trate was washed with THF (3 ×5 mL). The resulting organic frac- tions were combined, and THF was removed under reduced pres- sure to afford the crude amides. Recrystallization from hexanes and drying in a vacuum produced the desired product (4a-4e) [11] .
82% With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere; To a solution of 2-iodoaniline (23.6 g, 108 mmol) in DCM (250 mL) was added TEA (13.1 g, 129 mmol) and cooled to 0 C. Then acetylchloride (9.30 g, 119 mmol) was added to the reaction mixture at 0 C. by dropwise and stirred at 20 C. for 2 hours. On completion, the reaction mixture was quenched by water (200 mL) and extracted with dichloromethane (3×100 mL). The extracts was washed by brine (100 mL) and dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to get the crude residue. The residue was purified by column chromatography (SiO2, petroleum ether:dichloromethane:ethyl acetate=1:0:0 to 10:5:1) to give the title compound (25 g, 82% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.21 (d, J=7.6 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.48 (s, 1H) 7.35 (td, J1=1.2 Hz, J2=8.4 Hz, 1H), 6.85 (t, J=7.2 Hz, 1H), 2.25 (s, 3H); LC-MS (ESI, m/z): [M+1]+=261.7.
54% In toluene; at 20℃; for 3h; General procedure: To a solution of o-iodoaniline(2 mmol) in dry toluene (10 mL), acid chloride (2.4 mmol) was addedand the resulting mixture was stirred at room temperature for 3 h. Then, dichloromethane(20 mL) and HCl (1N, 20 mL) were added. The organic layer was separated and driedover anhydrous Na2SO4 and concentrated. The crude residuewas purified by column chromatography.
With pyridine; at 0 - 20℃; for 3h; Example 37; 2-Cyclopropyl-l-[4-(3-pyrrolidin-l-ylpropoxy)phenyl]-li-indoIe; iV~(2-Iodophenyl)acetamide; 2-Iodoaniline (1.00 g, 4.56 mmol) was dissolved in pyridine (5 mL) and cooled to 0 C. After acetyl chloride (314 μL5 5.94 mmol) was added, the reaction was stirred at 0 C for 1 hour and then at room temperature for 2 hours. The reaction was diluted with 1 N HCl and extracted with ether. The organic layer was dried (MgSO4) and EPO <DP n="38"/>concentrated to give the desired acetamide (assumed quantitative), which was used in the next reaction without further purification.
In dichloromethane; at 20℃; for 24h; General procedure: To a solution of o-haloaniline (4.63 mmol) in dry DCM (20 mL) at room temperature was dropped acyl chloride (5.09 mmol). The reaction mixture was stirred for 24 hours then poured into water, extracted with DCM, washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. The product was carried on to next step without any further purification in most cases.
With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 0.666667h; General procedure: The procedure consists of two steps. First, to a stirred, cooled (0-5C) solution of 2-bromoaniline (2.190g, 10mmol) and Et3N (1.113g, 1.55ml, 11mmol) in 20ml of dry THF, a solution of an appropriate acyl chloride (10mmol) in 5ml of dry THF was added dropwise within 10min. Then the ice bath was removed and the mixture was stirred vigorously for 30min at room temperature. Then, solid Et3NHCl was filtered off and washed with THF (3×5ml). The resulting organic fractions were combined and THF was removed under reduced pressure to yield crude amides. Recrystallization from hexane/CHCl3 and drying in vacuum afforded the analytically pure intermediate compounds: N-(2-bromophenyl)acylamides. In the second step, to a stirred suspension of NaH (0.132g; 5.5mmol) in 5ml of dry THF at 0C the respective amide (5mmol) dissolved in 10ml of THF was added dropwise within 10min. The reaction mixture was stirred until the solution became clear (30min, hydrogen gas evolved), and the solution of MeI (0.923g; 0.405ml; 6.5mmol) in 5ml of THF was added dropwise within 10min. The solution was warmed up to room temperature and stirred for 3-8h. Then, the reaction mixture was quenched with water (30ml). The resulting solution was extracted with ethyl acetate (3×20ml). Combined organic layers were washed with brine (1×20ml) and dried over Na2SO4. Ethyl acetate was removed under reduced pressure to give crude 1a-r. Recrystallization from hexane and drying in vacuum afforded analytically pure compounds 1a-r. In the case of (1n) and (1o), the same procedure was conducted but instead of MeI, ethyl bromide and benzyl bromide were respectively used. In the case of (1p), 2-bromopyridin-3-amine was used instead of 2 bromoaniline. In the case of (1a-Cl) and (1a-I), the same procedure was conducted but instead 2-bromoaniline, 2-chloro- and 2-iodoaniline were respectively used.

  • 12
  • [ 19591-17-4 ]
  • [ 142-29-0 ]
  • [ 126087-55-6 ]
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