Indole-3-Carboxylic Acid → 1-(4-Methoxy-naphthalene-1-sulfonyl)-1H-indole-3-carboxylic Acid

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Reaction Steps

To a solution of 1H-indole-3-carboxylic acid (0.5 g, 3.1 mmol) in tetrahydrofuran (20 cm3 at 0° C. was added sodium bis(trimethylsilyl)amide (6.2 cm3, 6.2 mmol) dropwise under nitrogen. The solution was stirred at 0° C. for 30 m before addition of 4-methoxy-1-naphthyl sulfonyl chloride (0.8 g, 3.1 mmol) and the resultant solution was stirred at room temperature for 18 h. The solution was diluted with saturated aqueous sodium bicarbonate solution and washed with ethyl acetate. The aqueous layer was acidified to pH 1 with 5N hydrochloric acid and the product extracted into ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to give the title compound (A) (1.1 g, 93%).

Provenance & Evidence