4-Methoxycarbonylphenylboronic acid → HCID 22616369, compound

Participants

Reaction Steps

A mixture of 2-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-6,7-dihydro-5H-benzocyclohepten-8-carboxamide (0.95 g) and 4-methoxycarbonylphenylboronic acid (0.4 g) in 1M potassium carbonate (6 ml), ethanol (6 ml) and toluene (75 ml) was stirred for 30 minutes at room temperature under argon. Tetrakis(triphenylphosphine)palladium (0.12 g) was added to the mixture, and the mixture was refluxed for 6 hours under argon. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over MgSO4. The solvent was evaporated in vacuo. The residue was subjected to a silica gel column chromatography (ethyl acetate/methanol/triethylamine) to give 2-(4-methoxycarbonylphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-6,7-dihydro-5H-benzocyclohepten-8-carboxamide (0.4 g) as colorless prisms.

Provenance & Evidence