Sodium hydride → HCID 10413115, compound

Participants

Reaction Steps

To a mixture of sodium hydride (37 mg, 1.54 mmol) in 3 mL of dimethylsulfoxide is added 2-thiophenemethanol (48 mg, 0.42 mmol). The solution is stirred at room temperature for 45 minutes. 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile (150 mg, 0.38 mmol) is added and the reaction mixture is heated at 100° C. overnight, then cooled to room temperature. The reaction mixture is poured into saturated sodium bicarbonate and the solids are collected by filtration. Purification by flash column chromatography eluting with 1:1 hexane:ethyl acetate provides 61 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-(2-thienylmethoxy)-3-quinolinecarbonitrile, mp 194-196° C.

Provenance & Evidence