2-溴-3-甲基-N-(2-苯乙基)苯甲酰胺

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Triflic anhydride (0.18 mL, 1.037 mmol) was added via syringe over 1 min to a stirred mixture of 2-bromo-3-methyl-N-phenethylbenzamide (0.30 g, 0.943 mmol) and 2-chloropyridine (0.11 mL, 1.131 mmol) in DCM (4.7 mL) at −78° C. The reaction mixture was stirred at −78° C. for 5 min, then placed in an ice-water bath and warmed to 0° C. After stirring another 5 min, the solution was allowed to warm to RT and then placed in a pre-heated block and stirred at 45° for 2 h. The reaction mixture was allowed to cool to RT, then it was diluted with 1N NaOH (3 mL) and extracted with DCM (15 mL). The organic extract was washed with saturated aqueous NaCl (2×15 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of 1-10% MeOH/DCM to provide 1-(2-bromo-3-methylphenyl)-3,4-dihydroisoquinoline as off-white glass. placed in an ice-water bath warmed to 0° C After stirring another 5 min to warm to RT stirred at 45° for 2 h to cool to RT extracted with DCM (15 mL) The organic extract was washed with saturated aqueous NaCl (2×15 mL) dried over Na2SO4 The solution was filtered concentrated in vacuo to give the crude material as a light-yellow oil The crude material was absorbed onto a plug of silica gel purified by column chromatography eluting with a gradient of 1-10% MeOH/DCM

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

实验步骤: To a solution of 2-phenethylamine (0.28 mL, 2.195 mmol) in DCM (2.0 mL) was added 2-bromo-3-methylbenzoyl chloride (0.15 mL, 0.998 mmol) dropwise via syringe at ambient temperature. Mixture was allowed to stir overnight, then diluted with water (30 mL) and extracted with DCM (30 mL). The organic extract was washed with 1N HCl (2×25 mL) and 1N NaOH (2×25 mL) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give 2-bromo-3-methyl-N-phenethylbenzamide as a white solid. extracted with DCM (30 mL) The organic extract was washed with 1N HCl (2×25 mL) and 1N NaOH (2×25 mL) dried over MgSO4 The solution was filtered concentrated in vacuo

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

实验步骤: To a solution of 2-phenethylamine (0.28 mL, 2.195 mmol) in DCM (2.0 mL) was added 2-bromo-3-methylbenzoyl chloride (0.15 mL, 0.998 mmol) dropwise via syringe at ambient temperature. Mixture was allowed to stir overnight, then diluted with water (30 mL) and extracted with DCM (30 mL). The organic extract was washed with 1N HCl (2×25 mL) and 1N NaOH (2×25 mL) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give 2-bromo-3-methyl-N-phenethylbenzamide as a white solid. extracted with DCM (30 mL) The organic extract was washed with 1N HCl (2×25 mL) and 1N NaOH (2×25 mL) dried over MgSO4 The solution was filtered concentrated in vacuo

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Triflic anhydride (0.18 mL, 1.037 mmol) was added via syringe over 1 min to a stirred mixture of 2-bromo-3-methyl-N-phenethylbenzamide (0.30 g, 0.943 mmol) and 2-chloropyridine (0.11 mL, 1.131 mmol) in DCM (4.7 mL) at −78° C. The reaction mixture was stirred at −78° C. for 5 min, then placed in an ice-water bath and warmed to 0° C. After stirring another 5 min, the solution was allowed to warm to RT and then placed in a pre-heated block and stirred at 45° for 2 h. The reaction mixture was allowed to cool to RT, then it was diluted with 1N NaOH (3 mL) and extracted with DCM (15 mL). The organic extract was washed with saturated aqueous NaCl (2×15 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of 1-10% MeOH/DCM to provide 1-(2-bromo-3-methylphenyl)-3,4-dihydroisoquinoline as off-white glass. placed in an ice-water bath warmed to 0° C After stirring another 5 min to warm to RT stirred at 45° for 2 h to cool to RT extracted with DCM (15 mL) The organic extract was washed with saturated aqueous NaCl (2×15 mL) dried over Na2SO4 The solution was filtered concentrated in vacuo to give the crude material as a light-yellow oil The crude material was absorbed onto a plug of silica gel purified by column chromatography eluting with a gradient of 1-10% MeOH/DCM

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

实验步骤: To a solution of 2-phenethylamine (0.28 mL, 2.195 mmol) in DCM (2.0 mL) was added 2-bromo-3-methylbenzoyl chloride (0.15 mL, 0.998 mmol) dropwise via syringe at ambient temperature. Mixture was allowed to stir overnight, then diluted with water (30 mL) and extracted with DCM (30 mL). The organic extract was washed with 1N HCl (2×25 mL) and 1N NaOH (2×25 mL) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give 2-bromo-3-methyl-N-phenethylbenzamide as a white solid. extracted with DCM (30 mL) The organic extract was washed with 1N HCl (2×25 mL) and 1N NaOH (2×25 mL) dried over MgSO4 The solution was filtered concentrated in vacuo