Ethanol → methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

In toluene (200 ml) and ethanol (35 ml) were suspended methyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (5.0 g), 4-butoxyethoxyphenyl borate (4.6 g) and 1M potassium carbonate solution (35 ml), and the mixture was stirred for 30 minutes under argon atmosphere. Then, to the mixture was added tetrakistriphenylphosphinepalladium (1 g), and the mixture was heated at 100° C. overnight under argon atmosphere. After allowing to cool, to the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed a with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1) to give the solid, which was washed with hexane to give methyl 7-(4-butoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate (5.7 g) as yellow crystals.

Provenance & Evidence