Cesium carbonate → 6-Cyano-4-(4-fluoro-2-methylindol-5-yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinoline

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-chloro-6-cyano-7-(3-(pyrrolidin-1-yl)propoxy)quinoline (500 mg, 1.58 mmol), 4-fluoro-5-hydroxy-2-methylindole (314 mg, 1.9 mmol) and cesium carbonate (775 mg, 2.38 mmol) in DMF (15 ml) was heated at 95° C. for 2 hours. After removal of the volatiles by evaporation under vacuum, the residue was dissolved in methylene chloride and poured onto a column of silica and eluted with a mixture of methylene chloride/methanol (90/10) followed by methylene chloride/methanol/methanol saturated with ammonia (88/10/2). The fractions containing the expected product were combined and evaporated to give 6-cyano-4-(4-fluoro-2-methylindol-5-yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinoline (558 mg, 79%).

Provenance & Evidence