Cesium carbonate → 2,3,4,5-Tetrahydro-1H-benzo(d)azepine

Participants

Reaction Steps

Use a method similar to the General Procedure 1-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (93.5 mg, 0.2 mmol) with 4-[5-(3,3-dimethylbutyryl)tiophen-2-yl]-benzylamine (129 mg, 0.4 mmol) using tris(dibenzylideneacetone)dipalladium(0) (40.3 mg, 0.04 mmol), BINAP (58.3 mg, 0.08 mmol) and cesium carbonate (100 mg, 0.3 mmol) in toluene/DMF (11:1, 12 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (4:1) to give 7-chloro-6-{4-[5-(3,3-dimethylbutyryl)-tiophen-2-yl]-benzylamino}trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (77 mg, 62%). MS (ES+) m/z: 563 (M+H)+.

Provenance & Evidence