N-(but-3-yn-1-yl)pivalamide → 7-chloro-6-[4-(2,2-dimethyl-propionylamino)-but-1-ynyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Participants

Reaction Steps

Use a method similar to the General Procedure 3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (425 mg, 1 mmol) with N-but-3-ynyl-2,2-dimethyl-propionamide (306 mg, 2 mmol) in DMF (10 mL). Purify by chromatography on silica gel eluting with cyclohexane/EtOAc (85:15 to 0:100 gradient) to obtain 7-chloro-6-[4-(2,2-dimethyl-propionylamino)-but-1-ynyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil (437 mg, 99%).

Provenance & Evidence