Isopropenyl acetate → 1-(4-Nitro-benzyl)-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Benzyl Ester

Participants

Reaction Steps

A solution of 5-bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid benzyl ester (1.733 g, 3.72 mmol), tributyltin methoxide (1.79 g, 1.6 ml, 5.58 mmol), isopropenyl acetate (0.56 g, 0.61 ml, 5.58 mmol), palladium (II) acetate (41.5 mg, 0.19 mmol) and tri-o-tolylphosphine (113 mg, 0.37 mmol) in toluene (5 ml) was heated at about 95° C. under nitrogen for about 6 hours. The reaction solution was cooled, concentrated in vacuo, and subjected to flash chromatography on silica (105 g, 30% ethyl acetate/hexanes). The partially pure product was re-chromatographed on silica (12 g, 50% methylene chloride/hexanes) to give the title compound (547 mg).

Provenance & Evidence