Cesium carbonate → HCID 86624181, compound

Participants

Reaction Conditions

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 (639 mg, 1.50 mmol) with 4-(2,2-dimethyl-propanesulfonylmethyl)-benzylamine (479 mg, 1.88 mmol), using tris(dibenzylideneacetone)dipalladium(0) (137 mg, 0.15 mmol), BINAP (187 mg, 0.3 mmol) and cesium carbonate (977 mg, 3 mmol) in toluene (20 mL). Heat the mixture at 90° C. overnight. Cool the mixture to room temperature and purify by chromatography on silica gel (80 g) eluting with hexane/EtOAc (1:0 to 4:1 gradient over 15 min; 50 mL/min) to give 7-chloro-6-[4-(2,2-dimethyl-propanesulfonyl-methyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (615 mg, 77%). MS (APCI+) m/z: 531 (M+H)+.

Provenance & Evidence