Methylboronic Acid → Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-7,8-dimethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

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Reaction Steps

Combine isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-7-bromo-8-methyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.058 g, 0.095 mmol), methylboronic acid (0.011 g, 0.190 mmol), palladium acetate (0.0009 g, 0.004 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.0036 g, 0.0087 mmol) and potassium phosphate monohydrate (0.044 g, 0.190 mmol) in toluene (2 mL) and heat in a sealed tube at 100° C. for 24 h. Dilute the cooled mixture with ethyl acetate (30 mL) 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 as a white solid (0.020 g, 38%): ESI MS 545 (M+H).

Provenance & Evidence