Tetrahydrofuran → Ethyl 1-[2-(acetylamino)ethyl]-6-methoxy-1H-indole-2-carboxylate

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Reaction Steps

Dissolve 0.34 g of the compound obtained in Step A in 10 ml of tetrahydrofuran and add a catalytic amount of Raney nickel and hydrogenate the reaction (10 bars) at ambient temperature for 24 hours. Filter over Celite and then evaporate. Take up the residue in 10 ml of tetrahydrofuran in the presence of 0.16 ml of triethylamine and, at 0° C. under argon, add dropwise 0.15 ml of acetic anhydride. Stir the reaction at ambient temperature for 22 hours. Evaporate, and take up the residue in ethyl acetate. Wash the organic phase with saturated aqueous sodium hydrogen carbonate solution and then with saturated aqueous sodium chloride solution and subsequently dry over sodium sulfate. Filter and evaporate in vacuo, and then purify the compound by column chromatography on silica gel using ethyl acetate as eluant. The title compound is isolated in the form of a white solid.

Provenance & Evidence