Ethanol → 1-allyl-7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

In toluene (15 ml), ethanol (1.5 ml) and water (1.5 ml) were suspended 1-allyl-7-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (262 mg), 4-butoxyethoxyphenyl borate (169 mg) and potassium carbonate (196 mg), and the suspension was stirred under argon atmosphere for 30 minutes. Then, to the mixture was added tetrakistriphenylphosphinepalladium (45 mg), and the mixture was heated under argon atmosphere at 100° C. for 6 hours. After allowing to cool, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was separated and purified with silica gel column chromatography (methanol:ethyl acetate=1:16), which was recrystallized from hexane-ethyl acetate to give 1-allyl-7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 50) (46 mg) as yellow crystals.

Provenance & Evidence