4-溴-N-环庚基苯甲酰胺

反应条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under a nitrogen atmosphere, add 6-aminomethyl-3-tert-butoxycarbonyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (500 mg, 1.6 mmol), 4-bromo-N-cycloheptyl-benzamide (520 mg, 1.8 mmol), palladium(II) acetate (35 mg, 0.16 mmol), BINAP (150 mg, 0.24 mmol) and sodium-t-butoxide (460 mg, 4.8 mmol) to toluene (10 mL). Heat the mixture at 70° C. for 1 h. Cool the mixture to room temperature and dilute with water and DCM. Separate the layers and extract the aqueous phase with DCM. Wash the combined organic extracts with water and brine. Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 17:1 gradient) to obtain 3-tert-butoxycarbonyl-7-chloro-6-[(4-cycloheptylcarbamoyl-phenylamino)-methyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (460 mg, 54%). MS (APCI+) m/z: 526 (M+H)+. Cool the mixture to room temperature Separate the layers extract the aqueous phase with DCM Wash the combined organic extracts with water and brine Dry the organic layer over Na2SO4 filter concentrate in vacuo Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 17:1 gradient)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dissolve 4-bromo-benzoyl chloride (2.0 g, 9.1 mmol) in DCM (20 mL). Cool the solution to 0° C. and add triethylamine (2.54 mL, 18.2 mmol) followed by cycloheptylamine (1.24 g, 10.9 mmol). Warm the mixture to room temperature over 1 h. Wash the mixture with saturated NaHCO3 (15 mL). Collect the organic layer, and extract the aqueous layer with DCM. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel (120 g) eluting with hexane/EtOAc (1:1) to obtain the title compound as a solid (2.5 g, 93%). MS (APCI+) m/z: 296 (M)+. Warm the mixture to room temperature over 1 h Wash the mixture with saturated NaHCO3 (15 mL) Collect the organic layer extract the aqueous layer with DCM Dry the combined organic extracts over Na2SO4 filter concentrate in vacuo Purify the residue by chromatography on silica gel (120 g) eluting with hexane/EtOAc (1:1)