Cesium carbonate → 1-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone

Participants

Reaction Conditions

Reaction Steps

Use a method similar to the General Procedure 5-2 to react 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (166 mg, 0.39 mmol), tris(dibenzylideneacetone)dipalladium(0) (71 mg, 0.078 mmol), BINAP (103 mg, 0.156 mmol), 3-aminomethyl-6-(3,3-dimethyl-butyl)-pyridine (150 mg, 0.78 mmol) and cesium carbonate (178 mg, 0.546 mmol) in degassed toluene (20 mL). Degas the mixture with vacuum/nitrogen purge and heat to 100° C. for 14 h. Cool the mixture to room temperature, dilute with EtOAc and filter through Celite®. Purify the crude mixture by chromatography on silica gel eluting with hexane and then hexane/EtOAc (19:1, 9:1 and 4:1) to obtain 7-chloro-6,6-(3,3-dimethyl-butyl)-pyridin-3-yl-methylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as oil (149 mg, 82%). MS (ES+) m/z: 468 (M+H)+.

Provenance & Evidence