Dichloromethane → HCID 22482337, compound

Participants

Reaction Steps

A stirred solution of 2-bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (Example 44, Step c, 0.25 g, 0.52 mmol) and phenylboronic acid (0.06 g, 0.52 mmol) in tetrahydrofuran (5 mL) was treated under nitrogen with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (0.01 g, 0.02 mmol) and a 5 N aqueous sodium hydroxide solution (0.2 mL, 1 mmol). The reaction mixture was heated at reflux for twelve hours, cooled to room temperature, and quenched with a saturated, aqueous, sodium chloride solution (10 mL) and diethyl ether (50 mL). The separated organic phase was dried over anhydrous magnesium 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 (1:4) to yield the title compound as a solid (0.13 g, 50%);

Provenance & Evidence