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

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Reaction Steps

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine 1 (638 mg, 2.51 mmole) was dissolved in DMF (30 mL) and sodium hydride (60% dispersion in mineral oil, 100 mg, 2.50 mmole) was added in small portions to the reaction mixture. After stirring for 30 minutes, 2-ethoxy-1-naphthoyl chloride (646 mg, 2.76 mmole) was added and the reaction was stirred for 4 hours. The reaction mixture was poured into 200 mL of ice water and was extracted with ethyl acetate. The organic layer was washed with saturated bicarbonate solution followed by saturated potassium hydrogen sulfate and then brine. The resulting solution was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate:hexanes) to yield 800 mg (70%) of the titled compound as a white solid MS(ESI) [M+H+]+=453.06.

Provenance & Evidence