Potassium Hydroxide → 7-Hydroxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid

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Reaction Steps

Ethyl 7-[(methylsulfonyl)oxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (1.56 g) was dissolved in a mixture of tetrahydrofuran (10 mL) and ethanol (15 mL). A solution of potassium hydroxide (85%, 0.8 g) in water (10 mL) was added to the mixture at 0° C. The mixture was allowed to warm to room temperature and stirred for 13 h. The mixture was concentrated under reduced pressure. The residue was dissolved in water and 1M hydrochloric acid (14 mL) was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether to give the title compound (0.93 g, 81%) as a pale orange solid. MS 349 (MH+).

Provenance & Evidence