Benzyl Alcohol → Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-benzyloxy-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

Participants

Reaction Steps

Combine isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.100 g, 0.168 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.0031 g, 0.0033 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.0043 g, 0.010 mmol), cesium carbonate (0.082 g, 0.252 mmol) and benzyl alcohol (0.035 mL, 0.336 mmol) in toluene (0.67 mL) in a sealed tube and heat at 110° C. for 20 h. Dilute the cooled mixture with dichloromethane (50 mL) and filter through Celite. Remove the filtrate solvent under reduced pressure and first purify the residue using chromatography on silica gel, eluting with hexanes/ethyl acetate (60:40), to provide the title compound as a white solid (0.054 g, 52%): ESI MS 623 (M+H).

Provenance & Evidence