N-bromobutanimide → (S)-(9-bromo-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(3-chloro-5-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amine

Participants

Reaction Steps

Stir (S)-(3-chloro-5-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-5-yl)-amine (0.53 g, 1.02 mmol) with N-bromosuccinimide (0.22 g, 1.22 mmol) in acetic acid (2 mL) at room temperature for 2 h. Evaporate the solvent under reduced pressure. Dilute the residue with water and neutralize with saturated NaHCO3 and extract with EtOAc (3×25 mL). Combine the organic layers and wash with water and brine, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography, eluting with hexane/ethyl acetate (5-40% EtOAc in hexane), to provide the title compound (0.49 g, 83%). MS (ES+): 599 (M+H).

Provenance & Evidence