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CAS No. : | 1256823-89-8 | MDL No. : | MFCD18255326 |
Formula : | C8H8BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RUXHXSRABFBHKZ-UHFFFAOYSA-N |
M.W : | 214.06 | Pubchem ID : | 84680121 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.1 |
TPSA : | 29.96 Ų |
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) : | -6.45 cm/s |
Log Po/w (iLOGP) : | 1.95 |
Log Po/w (XLOGP3) : | 1.63 |
Log Po/w (WLOGP) : | 2.36 |
Log Po/w (MLOGP) : | 1.2 |
Log Po/w (SILICOS-IT) : | 2.78 |
Consensus Log Po/w : | 1.98 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.53 |
Solubility : | 0.629 mg/ml ; 0.00294 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.87 |
Solubility : | 2.88 mg/ml ; 0.0134 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.61 |
Solubility : | 0.0529 mg/ml ; 0.000247 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.64 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 1,2-dichloro-ethane / 18 h / 60 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; dichloromethane / 18 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 1,2-dichloro-ethane / 18 h / 60 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; dichloromethane / 18 h / 85 °C 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 4 h / 80 °C 3.2: 0.5 h 4.1: potassium carbonate / N,N-dimethyl-formamide / 16 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 1,2-dichloro-ethane / 18 h / 60 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; dichloromethane / 18 h / 85 °C 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 4 h / 80 °C 3.2: 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 1,2-dichloro-ethane / 18 h / 60 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; dichloromethane / 18 h / 85 °C 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 4 h / 80 °C 3.2: 0.5 h 4.1: potassium carbonate / N,N-dimethyl-formamide / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 1,2-dichloro-ethane / 18 h / 60 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; dichloromethane / 18 h / 85 °C 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 4 h / 80 °C 3.2: 0.5 h 4.1: potassium carbonate / N,N-dimethyl-formamide / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 1,2-dichloro-ethane / 18 h / 60 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; dichloromethane / 18 h / 85 °C 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 4 h / 80 °C 3.2: 0.5 h 4.1: potassium carbonate / N,N-dimethyl-formamide / 16 h 5.1: Lux Cl, 5 micron, 4.6 x 250 mm, Phenomenex Inc. / methanol; carbon dioxide / Supercritical conditions; Resolution of racemate; liquid CO2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 1,2-dichloro-ethane / 18 h / 60 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; dichloromethane / 18 h / 85 °C 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 4 h / 80 °C 3.2: 0.5 h 4.1: potassium carbonate / N,N-dimethyl-formamide / 100 °C 5.1: ammonia / methanol; carbon dioxide / Supercritical conditions; Resolution of racemate; liquid CO2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / 1,2-dichloro-ethane / 18 h / 60 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; dichloromethane / 18 h / 85 °C 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 4 h / 80 °C 3.2: 0.5 h 4.1: potassium carbonate / N,N-dimethyl-formamide / 100 °C 5.1: ammonia / methanol; carbon dioxide / Supercritical conditions; Resolution of racemate; liquid CO2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.96 g | With (bis-(2-methoxyethyl)amino)sulfur trufluoride In 1,2-dichloro-ethane at 60℃; for 18h; | 1 Intermediate 50, 3-(1 , 1-difluoroethyl)-2-methyl-5-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)pyridine Step 1) Bis(2-methoxyethyl)aminosulfur trifluoride (50% in PhMe, 43.2 mL, 117.2 mmol) was added to a solution of 1-(5-bromo-2-methyl-3-pyridinyl)ethanone (Intermediate 49, 8.40 g, 39.2 mmol) in DCE (60 mL), the reaction mixture was stirred at 60°C for 18 h, then cooled to rt and quenched with MeOH (25 mL). The mixture was basified with saturated aqueous NaHCO3 to pH 8-9 and extracted with DCM (3 x 200 mL). The combined organic phases were dried (Mg504), concentrated in vacuo, and purified by gradient flash column chromatography, eluting with 0-20% EtOAc in petroleum ether, to yield 5 -bromo-3 -(1,1 -difluoroethyl)-2-methylpyridine (5.96 g, 25.2 mmol) as a yellow oil.LCMS (Method 2): m/z 238.0 (ES+), at 1.76 mm.1H NMR: (500 IVIHz, CDC13) : 1.95 (t, J=18.3, 3H), 2.63 (t, J=2.0, 3H), 7.88 (d, J=2.2, 1H), 8.59 (d, J=2.2, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.6 g | In tetrahydrofuran; diethyl ether at 0 - 15℃; for 3h; | 41.2 Step 2: preparation of l-(5-bromo-2-methyl-3-pyridyl)ethanone (compound 41c) To a solution of 5-bro mo- /V-methoxy-/V,2-di methyl-pyridine- 3-carboxamide (compound 41b, 2.40 g, 9.26 mmol) in THF (40 mL) was added methylmagnesium bromide (3.0 M in diethyl ether, 4.63 mL, 13.89 mmol) at 0 °C. After being stirred at 15 °C for 3 hrs, the reaction was quenched by addition of aq. NH4Cl (40 mL), diluted with water (60 mL) and extracted with EtOAc (40 mL) three times. The combined organic layer was washed with water (50 mL) twice and brine (30 mL) once, dried over Na2S04, concentrated and purified by flash column (PE:EtOAc = 10:1) to give compound 41c (1.60 g) as a colorless oil. MS: calc’d 214 (MH+), measured 214 (MH+). |
9 g | In tetrahydrofuran at 0℃; for 1h; | 1.2 Step 2. 1-(5-Bromo-2-methylpyridin-3-yl)ethenone Methylmagnesium bromide (3 M, 21.2 ml_) was added to a solution of 5-bromo-N-methoxy-N,2- dimethylnicotinamide (11 g, 42.4 mmol) in THF (100 ml_) at 0 °C. The reaction mixture was stirred at 25 °C for 1 hr. The reaction mixture was poured into saturated aq. NH4CI (400 ml_) and extracted with EA (400 ml_ x 2). The combined organic layer was dried over anhydrous Na2SC>4, filtered, and concentrated in vacuo. The residue was purified by FCC (Eluent: PE:EA = 1 :0 to 5:1) affording the title compound (9 g, 41.5 mmol) as yellow oil.LCMS (ESI) m/z: [79BrM+H]+ = 214.0.1H NMR (400 MHz, CDCI3) d = 8.66 (d, J = 2.4 Hz, 1 H), 8.06 (d, J = 2.0 Hz, 1 H), 2.70 (s, 3H), 2.60 (s, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
700 mg | With N-chloro-succinimide; 2,2'-azobis(isobutyronitrile) In acetonitrile at 80℃; for 16h; | 41.3 Step 3: preparation of l-[5-bromo-2-(chloromethyl)-3-pyridyl]ethanone (compound 41d) To a solution of l-(5-bromo-2-methyl-3-pyridyl)ethanone (compound 41c, 1.50 g, 7.01 mmol) in acetonitrile (30 mL) was added NCS (1.50 g, 11.24 mmol) and AIBN (173 mg, 1.05 mmol). After being stirred at 80 °C for 16 hrs, the reaction was quenched by addition of aq.NH4Cl (40 mL), diluted with water (60 mL) and extracted with EtOAc (50 mL) three times. The combined organic layer was washed with water (50 mL) twice and brine (30 mL) once, dried over Na2S04, concentrated and purified by flash column to give compound 41d (700 mg) as a colorless oil. MS: calc’d 248 (MH+), measured 248 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-chloro-succinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 16 h / 80 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-chloro-succinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 16 h / 80 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 3: thionyl chloride / dichloromethane / 18 h / 0 - 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-chloro-succinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 16 h / 80 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 3: thionyl chloride / dichloromethane / 18 h / 0 - 15 °C 4: potassium carbonate / ethanol / 3 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-chloro-succinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 16 h / 80 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 3: thionyl chloride / dichloromethane / 18 h / 0 - 15 °C 4: potassium carbonate / ethanol / 3 h / 65 °C 5: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 3 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-chloro-succinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 16 h / 80 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 3: thionyl chloride / dichloromethane / 18 h / 0 - 15 °C 4: potassium carbonate / ethanol / 3 h / 65 °C 5: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 3 h / 110 °C / Inert atmosphere 6: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 18 h / 0 - 45 °C 2: tetrahydrofuran; diethyl ether / 3 h / 0 - 15 °C | ||
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 25 °C 1.2: 14 h / 25 °C 2.1: tetrahydrofuran / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / ethanol; 1,2-dimethoxyethane / 14 h / 0 - 25 °C 2: sodium hydrogencarbonate / dimethyl sulfoxide / 14 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium <i>tert</i>-butylate / ethanol; 1,2-dimethoxyethane / 14 h / 0 - 25 °C 2: sodium hydrogencarbonate / dimethyl sulfoxide / 14 h / 25 °C 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 4 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium <i>tert</i>-butylate / ethanol; 1,2-dimethoxyethane / 14 h / 0 - 25 °C 2: sodium hydrogencarbonate / dimethyl sulfoxide / 14 h / 25 °C 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 4 h / 80 °C 4: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / ethanol; 1,2-dimethoxyethane / 14 h / 0 - 25 °C 2.1: sodium hydrogencarbonate / dimethyl sulfoxide / 14 h / 25 °C 3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 4 h / 80 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C 5.1: palladium diacetate; potassium carbonate; 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; water / dimethyl sulfoxide / 16 h / 100 °C / 775.74 Torr 5.2: DAICEL CHIRALPAK AD / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7 g | With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane; ethanol at 0 - 25℃; for 14h; | 1.3 Step 3. 2-(5-Bromo-2-methylpyridin-3-yl)propanenitrile tBuOK (9.23 g, 82.2 mmol) was added to a solution of 1-(5-bromo-2-methylpyridin-3-yl)ethenone (8 g, 37.4 mmol) and 1-(isocyanomethylsulfonyl)-4-methylbenzene (11.0 g, 56.1 mmol) in DME (400 ml_) and EtOH (16 ml_) at 0 °C. The reaction mixture was stirred at 25 °C for 14 hrs. The reaction mixture was poured into saturated aq. NhUCI (400 ml_). The mixture was concentrated in vacuo to remove DME and EtOH. The aqueous phase was extracted with EA (400 ml_ x 2). The combined organic layer was dried over anhydrous Na2S04, filtered, and concentrated in vacuo. The residue was purified by FCC (Eluent: PE:EA = 1 :0 to 5:1) affording the title compound (7 g, 31 .1 mmol) as colorless oil.LCMS (ESI)3m/z: [79BrM+H]+ = 225.1.1H NMR (400 MHz, CDCI3) d = 8.55 (d, J = 2.4 Hz, 1 H), 7.89 (d, J = 2.0 Hz, 1 H), 4.03 - 3.98 (m, 1 H), 2.57 (s, 3H), 1 .66 (d, J = 7.2 Hz, 3H) ppm. |
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