Benzylamine → 6-benzylamino-7-cyano-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 5-1 to couple 7-cyano-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (125 mg, 0.3 mmol) with benzylamine (0.1 mL, 0.9 mmol) using palladium(II) acetate (7 mg, 0.03 mmol), BINAP (37 mg, 0.06 mmol) and cesium carbonate (137 mg, 0.4 mmol) in toluene (3 mL). Purify by chromatography on silica gel eluting with heptane/EtOAc (4:1 to 1:1) to give 6-benzylamino-7-cyano-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a clear oil (60 mg, 54%). MS (ES+) m/z: 374 (M+H)+.

Provenance & Evidence