Hydrochloric Acid → Methyl 7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate

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Reaction Conditions

Reaction Steps

Methyl 7-hydroxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (1.1 g) was dissolved in a mixture of ethyl acetate (20 mL) and methanol (5 mL). The mixture was cooled to 0° C., and 2M trimethylsilyldiazomethane diethyl ether solution (2 mL) was added dropwise to the mixture. The mixture was stirred at 0° C. for 30 min, and then 2M trimethylsilyldiazomethane diethyl ether solution (0.5 mL) was added dropwise to the mixture again. After stirring at 0° C. for 30 min, 1M hydrochloric acid (1 mL) was added to the mixture to quench the reaction. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual oil was solidified with diethyl ether to give the title compound (0.99 g, 88%) as a pale orange solid. MS 377 (MH+).

Provenance & Evidence