Morpholine → Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-morpholin-4-yl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

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Reaction Steps

Combine tris(dibenzylideneacetone)dipalladium (0) (0.015 g, 0.017 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphyl (0.031 g, 0.050 mmol) and sodium t-butoxide (0.023 g, 0.235 mmol) in toluene (3 mL) in a 10 mL microwave vessel and purge this suspension with nitrogen at room temperature for 5 min. Add morpholine (0.016 mL, 0.185 mmol) followed by isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.100 g, 0.168 mmol) and irradiate this mixture at 110° C. for 15 min. Dilute the cooled mixture with dichloromethane and filter through Celite. Remove the filtrate solvent under reduced pressure and purify the residue using chromatography on silica gel, eluting with hexanes/ethyl acetate (60:40), to provide the title compound a yellow solid (0.041 g, 40%): ESI MS 602 (M+H)

Provenance & Evidence