Potassium Iodide → Ethyl 5-acetoxy-N-(3-methoxy-4-chlorobenzyl)indole-2-carboxylate

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Reaction Steps

To a solution of ethyl 5-acetoxyindole-2-carboxylate (283 mg) in DMF (6 ml) was added sodium hydride (54 mg, 60% dispersion in oil). The mixture was stirred for 30 minutes, a catalytic amount of potassium iodide and a solution of 3-methoxy-4-chlorobenzyl bromide (345 mg) in DMF (2 ml) was added. The mixture was stirred for 2 hours, quenched with water and extracted with ethyl acetate. The organic extracts were dried, evaporated and the resulting gum was purified by column chromatography elutig with 20% ethyl acetate/isohexane to give the desired product as an oil which solidified on standing (310 mg, 63%). NMR (CDCl3): d 1.4 (t, 3H), 2.3 (s, 3H), 3.8 (s, 3H), 4.35 (q, 2H, 5.8 (s, 2H), 6.5 (dd, 1H), 6.7 (d, 1H), 7.05 (dd, 1H), 7.2-7.4 (m, 4H); m/z 402 (M+H+).

Provenance & Evidence