9-Benzenesulfonyl-3-bromo-5-[1-(2,2-difluoroethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile → 9-Benzenesulfonyl-5-[1-(2,2-difluoroethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Participants

Reaction Steps

A suspension of 9-benzenesulfonyl-3-bromo-5-[1-(2,2-difluoroethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (240 mg, 0.42 mmol) and palladium on carbon (10 wt %, 50 mg) in industrial methylated spirits (5 mL) and dichloromethane (5 mL) was stirred at ambient temperature under an atmosphere of hydrogen for 5 days. The reaction vessel was purged with nitrogen then the reaction mixture was filtered through a PTFE filter cup. The filtrate was evaporated in-vacuo and the resultant residue purified by flash chromatography (silica, 10 g column, ISCO, 0-2% methanol in dichloromethane) to afford the title compound as an off-white solid (66 mg, 32%). LCMS (Method B): RT=3.74 min, M+H+=518.

Provenance & Evidence