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[ CAS No. 7746-27-2 ] {[proInfo.proName]}

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Chemical Structure| 7746-27-2
Chemical Structure| 7746-27-2
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Quality Control of [ 7746-27-2 ]

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Product Details of [ 7746-27-2 ]

CAS No. :7746-27-2 MDL No. :MFCD08272244
Formula : C8H7BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :PUVRYFUBGFMXMW-UHFFFAOYSA-N
M.W : 211.06 Pubchem ID :21336465
Synonyms :

Calculated chemistry of [ 7746-27-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.76
TPSA : 28.68 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 2.64
Log Po/w (WLOGP) : 2.63
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 2.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.42
Solubility : 0.0808 mg/ml ; 0.000383 mol/l
Class : Soluble
Log S (Ali) : -2.89
Solubility : 0.27 mg/ml ; 0.00128 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.16
Solubility : 0.0147 mg/ml ; 0.0000697 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 7746-27-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7746-27-2 ]

* 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 [ 7746-27-2 ]

[ 7746-27-2 ] Synthesis Path-Downstream   1~15

  • 2
  • [ 947685-09-8 ]
  • [ 7746-27-2 ]
YieldReaction ConditionsOperation in experiment
86% In ethylene glycol; at 165℃; for 6h; 1 -(4-Bromo-2-fluorophenyl)ethanone hydrazone (420 mg, 1.817 mmol) was dissolved in ethylene glycol (5 mL) and was heated at 165 C for 6 h after which time the cooled reaction mixture was poured into water (15 mL). The aqueous mixture was neutralized using a small amount of saturated aqueous sodium bicarbonate to afford a pale yellow precipitate. The solid was filtered, was washed with water and was dried to afford 6-bromo-3 -methyl- lH-indazole (330 mg, 86% yield) as a pale yellow solid. XH NMR (400 MHz, CDC13): delta 9.94 (br s, 1H), 7.60 (s, 1H), 7.53 (d, 1H), 7.23 (d, 1H), 2.62 (s, 3H).
78% In ethylene glycol; at 165℃; for 6h; The hydrazone (3.69 g, 16 mmol) was then treated with ethylene glycol (25 mL) and heated at 165 C. for 6 h after which time the cooled reaction mixture was poured onto water (100 mL). The aqueous mixture was neutralized, with rapid stirring, using a small amount of an aqueous saturated solution of NaHCO3 to afford a pale yellow precipitate. The solids were filtered, washed with water, and air dried to afford cyclized indazole product (2.62 g, 78%).
  • 3
  • [ 7746-27-2 ]
  • [ 75-36-5 ]
  • [ 1226985-37-0 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In acetonitrile; at 20℃; for 2h; Example 17: 14 Part A: Compound 722 (500 mg, 2.34 mmol) and acetyl chloride (278 mg, 3.52 mmol) were dissolved in acetonitrile (10 ml_) and pyridine (1 ml_) and stirred at room temperature for 2 hours. The reaction was quenched with 1 N HCI and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to provide compound 725 (520 mg).
  • 4
  • [ 625446-22-2 ]
  • [ 7746-27-2 ]
YieldReaction ConditionsOperation in experiment
72% With hydrazine hydrate; In ethylene glycol; at 165℃; for 12h; Intermediate 95 6-bromo-3-methyl-1H-indazole To a solution of intermediate 94 (3.7 g, 17.04 mmoles) in 1,2-ethanediol (25 ml), hydrazine hydrate (1.65 ml, 34.09 mmoles) was added at room temperature and heated to 165 C. After 12 h, the reaction mixture cooled to room temperature, quenched with water and solid precipitated was filtered and dried under vacuum to afford the title compound as colourless solid (2.5 g, 72% yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 12.74 (s, 1H), 7.67 (d, J=5.8 Hz, 1H), 7.65 (s, 1H), 7.19 (dd, J=8.6, 1.4 Hz, 1H), 2.46 (s, 3H).
With hydrazine hydrate; In ethylene glycol; at 20 - 200℃; for 1.5h;Microwave irradiation; Part C: Compound 721 (1.1 g, 5.04 mmol) was dissolved in ethylene glycol (10 ml_) and hydrazine monohydrate (277 mg, 5.5 mmol) and stirred at room temperature for 30 minutes followed by 1 hour at 200 0C in a microwave. The reaction was quenched with brine and extracted with methylene chloride. The organic layer was dried over sodium sulfate and concentrated to provide compound 722 (1.0 g). 1H NMR (400 MHz, CDCI3): delta 7.65 (m, 1 H), 7.58 (m, 1H), 7.3 (m, 1 H), 2.6 (S, 3H).
With hydrazine hydrate; In ethanol; at 120℃; for 23h; Intermediate 125; 6-Bromo-3-methyl-1 H-indazole; A suspension of 1-(4-bromo-2-fluorophenyl)ethanone (8.33 g, 38.4 mmol) in 15 mL of hydrazine monohydrate (309 mmol, 8 equiv) was heated to 120 0C under a reflux condenser for 23 hours. The resulting suspension (after cooling to room temperature) was filtered. The white solids were washed with water (2 X 15 mL), sucked under house vacuum at room temperature for 24 hours, and then dried under vacuum at room temperature over P2O5 for 24 hours to afford the title compound (7.59 g) as a yellow solid. LC-MS (ES) m/z = 211 , 213 [M+H]+.
With hydrazine hydrate; In ethylene glycol; at 200℃; for 4.5h;Microwave irradiation; [0001196] To a solution of l-(4-bromo-2-fluorophenyl)ethan-l-one (1.0 g, 3.89 mmol) in 1 ,2-ethanediol (12 mL) was added 80% of hydrazine monohydrate (0.6 mL, 7.78 mmol) at room temperature. The reaction mixture was stirred at 200 C in a microwave for 4.5 h, cooled down to room temperature, and quenched with water (50 mL). The solid precipitated was filtered, washed with water (20 mL), and dried under vacuo to afford Compound 334A.
With hydrazine hydrate; In ethanol; at 120℃; for 12h; [000673j A stirred solution of compound 3 (1 eq) in hydrazine monohydrate (8 eq) was stirred at 120 C for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with water, extracted with ethyl acetate (3 X 25 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was washed with diethyl ether to afford compound 4. LCMS (mlz): 213.00 (M+2).

  • 5
  • [ 7746-27-2 ]
  • [ 73183-34-3 ]
  • [ 1227911-51-4 ]
YieldReaction ConditionsOperation in experiment
91% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; dichloromethane; at 80℃; for 12.5h;Inert atmosphere; Intermediate 97 3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole To a solution of intermediate 95 (1.0 g, 4.73 mmoles) in Dioxan 16 ml), bis(pinacaloto)diboron (1.3 g, 5.21 mmoles) and potassium acetate (0.930 g, 9.47 mmoles) were added and the system is degassed for 30 min Bis(diphenylphosphinoferrocene)dichloro palladium.CH2Cl2 (0.387 g, 0.473 mmoles) was added under nitrogen atmosphere and heated to 80 C. After 12 h, the reaction mixture filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as off-white solid (1.1 g, 91% yield) which is used as such for the next step.
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere; Intermediate 126; 3-Methyl-6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-indazole; A mixture of <strong>[7746-27-2]6-bromo-3-methyl-1 H-indazole</strong> (8.32 g, 39.4 mmol), bis(pinacolato)diboron(11.01 g, 43.4 mmol, 1.1 equiv), potassium acetate (11.61 g, 118 mmol, 3 equiv) and PdCI2(dppf)?CH2CI2 adduct (1.61 g, 1.97 mmol, 0.05 equiv) in 1 ,4-dioxane (80 mL) was degassed and back flushed with argon. This action was repeated five times. The mixture was heated at 100 0C for 20 hours. After cooling to room temperature, the mixture was filtered through celite, and rinsed with EtOAc (200 mL). The filtrate was concentrated in vacuo, and the resulting residue was taken up in EtOAc (200 mL) and brine (50 mL), followed by filtration through celite. The filtrate was partitioned between phases, and the organic phase was treated with Darco and Na2SO4, filtered, and concentrated in vacuo. The residue was triturated in 30 mL of hexane, the resulting suspension was filtered, and the cake was washed with hexane (2 X 10 mL). Drying under vacuum at room temperature for 20 hours afforded the title compound (9.91 g) as a light pinkish solid. LC- MS (ES) m/z = 259 [M+H]+.
618 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 150℃; for 0.5h;Microwave irradiation; (1) Synthesis of 3-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dloxaborolan-2-yl)-1H-indazole [5-1] (hereinafter referred to as a compound [5-1]) To a solution of <strong>[7746-27-2]6-bromo-3-methyl-1H-indazole</strong> (647 mg), which was obtained by the method described in the document (JP 2009-528363 W), in 1,4-dioxane (10 mL) were added bis(pinacolato)diboron (1.15 g), potassium acetate (899 mg) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (126 mg), and the mixture was subjected to microwave irradiation at 150C for 30min. The reaction mixture was quenched with water, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (618 mg) as a yellow solid. 1H-NMR (400 MHz, CDCl3) delta: 7.93 (1H, s), 7.67 (1H, dd, J = 8.1, 0.7 Hz), 7.55 (1H, d, J = 8.3 Hz), 2.60 (3H, s), 1.37 (12H, s).
  • 6
  • [ 137-43-9 ]
  • [ 7746-27-2 ]
  • [ 947685-08-7 ]
YieldReaction ConditionsOperation in experiment
54% The indazole (2.32 g, 11 mmol) was then dissolved in anhydrous DMF (50 mL) and treated with a 60% dispersion of sodium hydride in mineral oil (420 mg, 10.5 mmol). After 30 min of stirring, cyclopentyl bromide (1.53 mL, 14.3 mmol) was added and the reaction stirred for 24 h. The reaction mixture was quenched by pouring onto water (500 mL) which was neutralized with a small portion of a 1 N aqueous HCl solution and extracted with EtOAc (2*200 mL, then 100 mL). The combined organic extracts were dried over MgSO4, filtered, and evaporated to an oil, which was purified by silica gel flash chromatography with 25% then 80% EtOAc/hexanes as eluant to afford product as a clear yellow tinted oil (1.65 g, 54%). 1H NMR (CDCl3) 1.68-1.78 (m, 2H), 1.93-2.01 (m, 2H), 2.08-2.16 (m, 4H), 2.54 (s, 3H), 4.77-4.87 (m, 1H), 7.18 (dd, J=8.4, 1.5, 1H), 7.32 (dd, J=8.4, 0.7, 1H), 7.55 (d, J=1.5, 1H). 13C NMR 12.1 (CH3), 24.7 (CH2), 32.2 (CH2), 59.5 (CH), 112.2 (CH), 120.5, 121.8 (CH), 122.5, 123.2 (CH), 141.1, 141.4. LC/MS 7.71 min, [M+1]+ 281.
  • 7
  • [ 57848-46-1 ]
  • [ 7746-27-2 ]
  • 8
  • [ 7746-27-2 ]
  • [ 74-88-4 ]
  • [ 1095539-84-6 ]
  • [ 1142189-49-8 ]
YieldReaction ConditionsOperation in experiment
Intermediate 114 6-bromo-1,3-dimethyl-1H-indazole(a) and 6-bromo-2,3-dimethyl-2H-indazole(b) To a solution of intermediate 95 (2 g, 9.47 mmoles) in THF (30 ml) cooled to 0 C., sodium hydride (0.454 g, 60% in paraffin oil, 11.37 mmoles) was added and stirred for 10 min. Methyl iodide (2.0 gl, 14.21 mmoles) was added warmed to room temperature. After 12 h, the reaction mixture cooled to room temperature, quenched with water, extracted with ethyl acetate and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as colourless solid. Fraction I (114a, 0.90 g, 43% yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 7.87 (d, J=1.0 Hz, 1H), 7.64 (d, J=9.5 Hz, 1H), 7.20 (dd, J=9.5, 1.5 Hz, 1H), 3.92 (s, 3H), 2.44 (s, 3H). Fraction II (114b, 0.80 g, 38% yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 7.72 (d, J=1.3 Hz, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.20 (dd, J=8.8, 1.6 Hz, 1H), 4.01 (s, 3H), 2.58 (s, 3H).
[0001206] To 6-bromo-3 -methyl- lH-indazole (1.9 g, 9.05 mmol) in DMF (15 mL) was added sodium hydride (60% in mineral, 398 mg, 9.96 mmol) with ice bath cooling. The mixture was stirred for 30 min at room temperature and iodomethane (0.94 mL, 27.15 mmol) was added. The reaction mixture was stirred at room temperature for 3 h, quenched with ammonium chloride solution (30 mL), and extracted with ethyl acetate (100 mL x 3). The combined organic layers were washed with brine (200 mL), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 90% v/v) to give Compound 340A and Compound 340B.
  • 9
  • [ 24424-99-5 ]
  • [ 7746-27-2 ]
  • [ 1300582-43-7 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine;dmap; In dichloromethane; at 0℃; for 3h; To a solution of 6- bromo-3 -methyl- lH-indazole (330 mg, 1.56 mmol) in dichloromethane (15 mL) was added triethylamine (0.67 mL, 4.68 mmol), di-tert-butyl dicarbonate (443 mg, 2.03 mmol) and 4- (dimethylamino)pyridine (19 mg, 0.156 mmol) at 0 C. The resulting solution was stirred for 3 h and the reaction mixture was washed with water, was dried over magnesium sulfate, was filtered and was concentrated. The residue was purified by column chromatography (eluted with ethyl acetate:hexanes = 1 :6) to give tert-butyl 6-bromo-3 -methyl- 1 H-indazole- 1- carboxylate (366 mg, 75% yield) as a light pink solid. ? NMR (400 MHz, CDC13): delta 8.31 (s, 1H), 7.46 (d, 1H), 7.37 (d, 1H), 2.54 (s, 3H), 1.60 (s, 9H).
70% Intermediate 96 tert-butyl <strong>[7746-27-2]6-bromo-3-methyl-1H-indazole</strong>-1-carboxylate To a solution of intermediate 95 (10.0 g, 47.39 mmoles) in acetonitrile (100 ml) cooled to 20 C., Boc-anhydride (10.3 g, 34.09 mmoles) was added followed by DMAP (0.579 g, 4.73 mmoles) and triethylamine (4.7 g, 47.39 mmoles) and the reaction mixture was stirred at room temperature. After 12 h, the reaction mixture was concentrated and quenched with water and solid precipitated was filtered and dried under vacuum to afford the title compound as colourless solid (10.3 g, 70% yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 8.19 (d, J=1.2 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H),), 7.54 (dd, J=8.5, 1.7 Hz, 1H), 2.50 (s, 3H), 1.62 (s, 9H).
  • 10
  • [ 353282-88-9 ]
  • [ 7746-27-2 ]
  • 11
  • [ 7746-27-2 ]
  • [ 1300584-82-0 ]
  • 12
  • [ 7746-27-2 ]
  • [ 1300584-95-5 ]
  • 13
  • [ 7746-27-2 ]
  • [ 1300585-01-6 ]
  • 14
  • [ 7746-27-2 ]
  • [ 1300585-02-7 ]
  • 15
  • [ 7746-27-2 ]
  • [ 1300585-03-8 ]
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