Ethanol → HCID 22329126, compound

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Reaction Steps

A mixture of methyl 7-bromo-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (20 g), 4-(2-ethoxyethoxy)phenyl borate (14.9 g), 1M potassium carbonate solution (130 ml), ethanol (130 ml) and toluene (1000 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium (3 g), and the mixture was refluxed under argon atmosphere for 15 hours and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 7-[4-(2-ethoxyethoxy)phenyl]-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (25.2 g) as colorless crystals.

Provenance & Evidence