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 (193 mg, 0.45 mmol) with 4-(1-cyclopropylmethyl-1H-pyrazol-3-yl)-benzylamine (207 mg, 0.91 mmol) using tris(dibenzylideneacetone)dipalladium(0) (83 mg, 0.091 mmol), BINAP (113 mg, 0.182 mmol) and cesium carbonate (207 mg, 0.627 mmol) in toluene (21 mL). Purify by chromatography on silica gel eluting with hexane:EtOAc (9:1) to give 7-chloro-6-[4-(1-cyclopropylmethyl-1H-pyrazol-3-yl)-benzylamino]trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (135 mg, 59%). MS (ES+) m/z: 503 (M+H)+.

Provenance & Evidence