Ethanesulfonyl chloride → tert-butyl 4-(3-(2-(2,4-difluorophenoxy)-5-(ethylsulfonamido)phenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)piperidine-1-carboxylate

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Reaction Steps

To a solution of Example 183B (205 mg, 0.363 mmol) in 10 mL dichloromethane was added N-ethyl-N-isopropylpropan-2-amine (254 μL, 1.452 mmol) and ethanesulfonyl chloride (120 μL, 1.271 mmol). The mixture was stirred at ambient temperature overnight. The mixture was concentrated. The viscous oil residue was taken into dioxane (10 mL) and treated with sodium hydroxide (5446 μL, 5.45 mmol, 1N aqueous solution). The mixture was stirred at ambient temperature for 80 minutes and then quenched with saturated ammonium hydroxide solution, and partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phases were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel with a gradient of 0-60% ethyl acetate in heptanes to give the title compound (110 mg, 0.167 mmol, 46.1% yield).

Provenance & Evidence