Ethyl Acrylate → HCID 53631951, compound

Participants

Reaction Steps

A solution of 0.75 g of 5-bromo-N-(3-pyridyl)indole and 0.5 g of ethyl acrylate in 20 ml of triethylamine is refluxed for 48 hours with 10.8 mg of palladium acetate and 30 mg of tri-o-tolylphosphine. The reaction mixture is cooled, evaporated and chromatographed on 20 g of silica gel with diethyl ether to yield 5-(2-ethoxycarbonylethenyl)-N-(3-pyridyl)indole. Saponification by refluxing for 15 hours in 30 ml of ethanol with 5 ml of 2N sodium hydroxide yields a solution which is evaporated to dryness. The residue is partitioned between 20 ml of ether and 10 ml of water. The aqueous phase is separated, brought to pH 5 and the resulting solid is filtered to yield 5-(2-carboxyethenyl)-N-(3-pyridyl)indole which melts with decomposition at 180°.

Provenance & Evidence