Ammonia → 5-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxamide

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Reaction Steps

A mixture of 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylic acid (1.0 g), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (0.9 g), 1-hydroxybenzotriazole (0.6 g) and N,N-dimethylformamide (15 mL) was stirred at room temperature for 15 min. 28% Aqueous ammonia solution (0.8 mL) was added to the reaction solution, and the mixture was stirred at room temperature for 2.5 hr. Water was added to the reaction solution, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was crystallized from a mixed solvent of ethanol-diethyl ether, and the obtained crystals were washed with diethyl ether to give the title compound (0.8 g, yield 83%) as colorless crystals. MS 445 (MH+).

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