Cesium carbonate → HCID 87119113, compound

Participants

Reaction Conditions

Reaction Steps

Use a method similar to the General Procedure 5-1 to react 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (3 g, 7.06 mmol), palladium(II) acetate (0.16 g, 0.71 mmol), BINAP (0.88 g, 1.41 mmol), 2,4-difluorobenzylamine (3.03 g, 21.18 mmol) and cesium carbonate (3.22 g, 9.88 mmol) in degassed toluene (120 mL). Degas the mixture with vacuum/nitrogen purge and heat to 100° C. for 16 h. Cool the mixture to room temperature, dilute with EtOAc, filter through Celite® and concentrate in vacuo to give a brown oil. Purify the crude mixture by chromatography on silica gel eluting with hexane and then hexane/THF (95:5) to obtain 7-chloro-6-(2,4-difluorobenzylamino)-3-(2,2,2,trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as oil (2.25 g, 76%). MS (ES+) m/z: 419 (M+H)+.

Provenance & Evidence