Cesium carbonate → HCID 86629694, compound

Participants

Reaction Steps

Use a method similar to the General Procedure 5-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (158 mg, 0.37 mmol) with 4-(2,2-dimethyl-propane-1-sulfonyl)-benzylamine (166 mg, 0.73 mmol) by using tris(dibenzylideneacetone)dipalladium(0) (68 mg, 0.074 mmol), BINAP (92 mg, 0.148 mmol) and cesium carbonate (169 mg, 0.518 mmol) in anhydrous toluene (15 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (8:2) and then by reversed HPLC [Zorbax Bonus RP, 5 □M 21.2×100 mm, eluting with water/acetonitrile (0.05% TFA in each), UV detector (230 nm)] to give 7-chloro-6-[4-(2,2-dimethyl-propane-1-sulfonyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil (153 mg, 80%). MS (ES+) m/z: 517 (M+H)+.

Provenance & Evidence