4-溴-2-N-苯基苯-1,2-二胺

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 5-bromo-N1-phenylbenzene-1,2-diamine (650 mg, 2.47 mmol) in HC(OMe)3 (15 mL) was added TsOH.H2O (38 mg, 0.2 mmol). The mixture was stirred at 100° C. for 4 h. Upon completion, the reaction solution was concentrated, the residue was extracted with EtOAc and washed with water. The organic layer was concentrated to give the crude 6-bromo-1-phenyl-1H-benzo[d]imidazole which was used in next step without further purification. LCMS (m/z): 273.1/274.1 [M+H]+/[M+2H]+ Upon completion, the reaction solution was concentrated the residue was extracted with EtOAc washed with water The organic layer was concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirred mixture of 4-bromo-N2-phenyl-benzene-1,2-diamine (step A) (420 mg, 1.6 mmol) and trimethyl orthoformiate (4.8 g, 5 ml, 45.2 mmol), formic acid (1.2 g, 1 ml, 26.1 mmol) was added at room temperature, and afterwards the reaction mixture was allowed to stir at for 2 h under reflux conditions. The reaction mixture was cooled to room temperature, evaporated and extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with sat. sodium bicarbonate solution (20 ml) and brine (20 ml), dried (MgSO4) and evaporated. The crude product (400 mg) was purified by flash chromatography on silica gel (heptane/ethyl acetate 3:2) to yield the title compound as an off-white solid (358 mg, 82%), MS (ISP) m/z=275.0 [(M+H)+]. was added at room temperature evaporated extracted with ethyl acetate (2×40 ml) The combined organic layers were washed with sat. sodium bicarbonate solution (20 ml) and brine (20 ml) dried (MgSO4) evaporated The crude product (400 mg) was purified by flash chromatography on silica gel (heptane/ethyl acetate 3:2)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirred mixture of 4-bromo-N2-phenyl-benzene-1,2-diamine (step A) (420 mg, 1.6 mmol) and trimethyl orthoformiate (4.8 g, 5 ml, 45.2 mmol), formic acid (1.2 g, 1 ml, 26.1 mmol) was added at room temperature, and afterwards the reaction mixture was allowed to stir at for 2 h under reflux conditions. The reaction mixture was cooled to room temperature, evaporated and extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with sat. sodium bicarbonate solution (20 ml) and brine (20 ml), dried (MgSO4) and evaporated. The crude product (400 mg) was purified by flash chromatography on silica gel (heptane/ethyl acetate 3:2) to yield the title compound as an off-white solid (358 mg, 82%), MS (ISP) m/z=275.0 [(M+H)+]. was added at room temperature evaporated extracted with ethyl acetate (2×40 ml) The combined organic layers were washed with sat. sodium bicarbonate solution (20 ml) and brine (20 ml) dried (MgSO4) evaporated The crude product (400 mg) was purified by flash chromatography on silica gel (heptane/ethyl acetate 3:2)

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 5-bromo-N1-phenylbenzene-1,2-diamine (650 mg, 2.47 mmol) in HC(OMe)3 (15 mL) was added TsOH.H2O (38 mg, 0.2 mmol). The mixture was stirred at 100° C. for 4 h. Upon completion, the reaction solution was concentrated, the residue was extracted with EtOAc and washed with water. The organic layer was concentrated to give the crude 6-bromo-1-phenyl-1H-benzo[d]imidazole which was used in next step without further purification. LCMS (m/z): 273.1/274.1 [M+H]+/[M+2H]+ Upon completion, the reaction solution was concentrated the residue was extracted with EtOAc washed with water The organic layer was concentrated

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 5-bromo-N1-phenylbenzene-1,2-diamine (650 mg, 2.47 mmol) in HC(OMe)3 (15 mL) was added TsOH.H2O (38 mg, 0.2 mmol). The mixture was stirred at 100° C. for 4 h. Upon completion, the reaction solution was concentrated, the residue was extracted with EtOAc and washed with water. The organic layer was concentrated to give the crude 6-bromo-1-phenyl-1H-benzo[d]imidazole which was used in next step without further purification. LCMS (m/z): 273.1/274.1 [M+H]+/[M+2H]+ Upon completion, the reaction solution was concentrated the residue was extracted with EtOAc washed with water The organic layer was concentrated