Sodium hydride → [4-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-(2-ethoxy-naphthalen-1-yl)-methanone

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Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 39.9 mg, 0.997 mmol) was washed with hexane and put under an atmosphere of nitrogen, and 1 mL of tetrahydrofuran was added. 4-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine (50, 195 mg, 0.767 mmol) in tetrahydrofuran (6.2 mL) was added, and the resulting mixture was stirred for 10 minutes at room temperature. 2-ethoxy naphthoyl chloride (202 mg, 0.844 mmol) in tetrahydrofuran was added. After two hours, the reaction was quenched with water, and the two layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded the crude material, which was purified by column chromatography (35-60% ethyl acetate in hexane) to yield the desired product in light yellow solid (48, 262 mg, 0.579 mmol). MS(ESI) [M+H+]+=453.2.

Provenance & Evidence