Ammonium Hydroxide → 7-(2-Methoxy-1-methylethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide

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A mixture of 7-(2-methoxy-1-methylethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid (1.40 g), 1-hydroxybenzotriazole (670 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.95 g) and N,N-dimethylformamide (50 mL) was stirred at room temperature for 30 min. An aqueous solution of ammonium hydroxide (25%, 5 mL) was added to the mixture. The whole was stirred at room temperature for 15 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was washed with ethyl acetate-hexane to give the title compound (1.35 g, 98%) as colorless crystals. MS 420 (MH+).

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