Cesium carbonate → HCID 86658974, compound

Participants

Reaction Conditions

Reaction Steps

Slurry 4-(2-methylamino-oxazol-4-yl)-benzylamine hydrochloride (485 mg, 1.8 mmol) in toluene (10 mL) and DMF (1 mL) at 90° C. under a nitrogen atmosphere. Degass and place under vacuum then purge with nitrogen three times. Add 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0:5 g, 1.17 mmol), tris(dibenzylideneacetone)dipalladium(0) (161 mg, 0.18 mmol), BINAP (219 mg, 0.35 mmol) and cesium carbonate (1.6 g, 4.9 mmol) to the slurry at 90° C. Stir the mixture at 95° C. for 16 h in a sealed flask. Cool the reaction to room temperature, dilute with EtOAc (100 mL), filter through Celite®, and concentrate in vacuo to an oil. Purify by chromatography on silica gel (10 g, pre-packed cartridge) eluting with hexane/THF (40:1 to 4:1 gradient) followed by SCX chromatography (10 g) eluting with DCM and DCM/2M ammonia in methanol (1:1, 50 mL) to obtain 7-chloro-6-[4-(2-methylamino-oxazol-4-yl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (110 mg, 20%). MS (ES+) m/z: 479.2 (M+H)+.

Provenance & Evidence