Water → HCID 66898207, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 7-hydroxy-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxylate (3.12 g) in a mixture of tetrahydrofuran (30 mL) and methanol (5 mL) was added dropwise 2M trimethylsilyldiazomethane diethyl ether solution (4.3 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, 2M trimethylsilyldiazomethane diethyl ether solution (8.0 mL) was added dropwise to the mixture again, and the mixture was stirred at 0° C. for 2.5 h. Furthermore, 2M trimethylsilyldiazomethane diethyl ether solution (4.0 mL) was added dropwise to the mixture, and the mixture was stirred at room temperature for 1 h. To quench the reaction, 6M hydrochloric acid (9 mL) was added to the mixture. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether to give the title compound (2.78 g, 86%) as a brown solid. MS 377 (MH+).

Provenance & Evidence