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CAS No. : | 1332527-03-3 | MDL No. : | MFCD27939304 |
Formula : | C14H11BrN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IBADFZNPMLMUBA-UHFFFAOYSA-N |
M.W : | 303.15 | Pubchem ID : | 67447175 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 15 |
Fraction Csp3 : | 0.07 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 75.26 |
TPSA : | 27.05 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.15 cm/s |
Log Po/w (iLOGP) : | 3.15 |
Log Po/w (XLOGP3) : | 4.23 |
Log Po/w (WLOGP) : | 3.8 |
Log Po/w (MLOGP) : | 3.92 |
Log Po/w (SILICOS-IT) : | 3.17 |
Consensus Log Po/w : | 3.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.87 |
Solubility : | 0.0041 mg/ml ; 0.0000135 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.51 |
Solubility : | 0.0094 mg/ml ; 0.000031 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.57 |
Solubility : | 0.000816 mg/ml ; 0.00000269 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.26 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate | ||
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; | 73.A Step A: 6-Bromo-3-methoxy-1-phenyl-1H-indazole Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-bromo-1-phenyl-1,2-dihydroindazol-3-one (5 g, 17.30 mmol, 1.00 equiv) in N,N-dimethylformamide (50 mL), potassium carbonate (3.7 g, 34.91 mmol, 2.00 equiv), CH3I (2.7 g, 19.01 mmol, 1.10 equiv). The resulting solution was stirred for 3 h at 80° C. in an oil bath. The reaction was then quenched by the addition of water (100 mL). The resulting solution was extracted with ethyl acetate (3*150 mL) and the organic layers combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:40) to yield 6-bromo-3-methoxy-1-phenyl-1H-indazole as a yellow solid. MS (m/z): 303 [M+H]+; 1HNMR (400 MHz, CDCl3, ppm): δ 4.168-4.183 (3H, d), 7.251-7.682 (7H, m), 7.837-7.839 (1H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 20 °C 2: caesium carbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 1.3: pH 7 2.1: hydrogenchloride; sodium nitrite / ethanol; water / 76 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / ethanol; water / 76 °C 2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.6% | With quinoline-2-carboxylic acid; potassium carbonate In dimethyl sulfoxide at 100℃; for 16h; | 6.3 General procedure: (3) The 6-bromo-3-methoxy-1H-indazole (66.35g, 0.29mol, 1.0eq) of compound 3 is dissolved in dimethyl sulfoxide (700mL),Add potassium carbonate (130.04g, 0.94mol, 3.22eq),Quinaldinic acid (4.02g, 23.2μmol, 0.08eq),Copper iodide (1.66g, 8.70μmol, 0.03eq)withBrominated benzene (55.06g, 0.35mol, 1.2eq). Under inert gas protection, heating at 100°C, reaction for 16 hours, TLC dot plate to monitor the completion of the reaction. Pour into ice water, extract with EA, spin dry, mix the sample and purify by column to obtain 6-bromo-3-methoxy-1-phenyl-1H-indazole of compound 4 (58.76g, 0.18mol, yield 66.18) %, the purity is 99.01%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.6% | With quinoline-2-carboxylic acid; potassium carbonate In dimethyl sulfoxide at 100℃; for 16h; | 7.3 General procedure: (3) The 6-bromo-3-methoxy-1H-indazole (66.35g, 0.29mol, 1.0eq) of compound 3 is dissolved in dimethyl sulfoxide (700mL),Add potassium carbonate (130.04g, 0.94mol, 3.22eq),Quinaldinic acid (4.02g, 23.2μmol, 0.08eq),Copper iodide (1.66g, 8.70μmol, 0.03eq)withBrominated benzene (55.06g, 0.35mol, 1.2eq). Under inert gas protection, heating at 100°C, reaction for 16 hours, TLC dot plate to monitor the completion of the reaction. Pour into ice water, extract with EA, spin dry, mix the sample and purify by column to obtain 6-bromo-3-methoxy-1-phenyl-1H-indazole of compound 4 (58.76g, 0.18mol, yield 66.18) %, the purity is 99.01%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium nitrate / trifluoroacetic anhydride / 0.5 h / 25 - 40 °C 2: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 3: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C | ||
Multi-step reaction with 3 steps 1: potassium nitrate / trifluoroacetic anhydride / 0.5 h / 25 - 40 °C 2: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 3: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C | ||
Multi-step reaction with 3 steps 1: potassium nitrate / trifluoroacetic anhydride / 0.5 h / 25 - 40 °C 2: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 3: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 2: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C | ||
Multi-step reaction with 2 steps 1: sodium methylate / N,N-dimethyl-formamide / 16 h / 20 °C 2: quinoline-2-carboxylic acid; potassium carbonate / dimethyl sulfoxide / 16 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.18% | With quinoline-2-carboxylic acid; potassium carbonate In dimethyl sulfoxide at 100℃; for 16h; | 1.3; 2.3; 3.3; 4.3; 5.3; 8.3; 9.3; 10.3; 11.3; 12.3 (3) The 6-bromo-3-methoxy-1H-indazole (66.35g, 0.29mol, 1.0eq) of compound 3 is dissolved in dimethyl sulfoxide (700mL),Add potassium carbonate (130.04g, 0.94mol, 3.22eq),Quinaldinic acid (4.02g, 23.2μmol, 0.08eq),Copper iodide (1.66g, 8.70μmol, 0.03eq)withBrominated benzene (55.06g, 0.35mol, 1.2eq). Under inert gas protection, heating at 100°C, reaction for 16 hours, TLC dot plate to monitor the completion of the reaction. Pour into ice water, extract with EA, spin dry, mix the sample and purify by column to obtain 6-bromo-3-methoxy-1-phenyl-1H-indazole of compound 4 (58.76g, 0.18mol, yield 66.18) %, the purity is 99.01%). |