Binap, (A+-)- → HCID 67337338, compound

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence