Pyridine → HCID 10345344, compound

Participants

Reaction Steps

A stirred solution of 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol (Example 40, Step d, 0.05 g, 0.13 mmol) in dichloromethane (2 mL) was treated sequentially with pyridine (0.04 mL, 0.52 mmol) and benzoyl chloride (0.03 mL, 0.26 mmol). After stirring for twelve hours and room temperature, the reaction was quenched with a saturated, aqueous sodium bicarbonate solution (50 mL). The separated aqueous phase was extracted with dichloromethane (3×10 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a crude product. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:9 to 1:4 gradient), followed by re-crystallization from a mixture of ethyl acetate-hexane, to yield the title compound as a white solid (0.04 g, 59%);

Provenance & Evidence