Triethylamine → (E)-3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-acrylic Acid Methyl Ester

Participants

Reaction Steps

WSCD (1.17 g, 6.16 mmol) was added to a solution of 4-((E)-2-methoxycarbonyl-vinyl)-benzoic acid from Example E65.1 (740 mg, 3.59 mmol), 2,3,4,5-tetrahydro-1H-benzo[b]azepine (445 mg, 3.02 mmol) and DMAP (370 mg, 3.02 mmol) in dichloromethane (40 ml) and triethylamine (0.7 ml, 5.02 mmol). The mixture was heated at reflux for 42 h then solvents were concentrated in vacuo. The residue was dissolved in EtOAc, washed with 1M KHSO4 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 30% EtOAc:70% pet. ether) to yield the title compound (484 mg, 48%).

Provenance & Evidence