Cesium carbonate → 4-(4-Fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnoline

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnoline (60 mg, 0.187 mmol), 4-fluoro-5-hydroxy-2-methylindole (46 mg, 0.28 mmol) and cesium carbonate (121 mg, 0.37 mmol) in DMA (2 ml) was heated at 100° C. for 2 hours. The volatiles were removed under vacuum and the residue was purified by column chromatography eluting with methanol/methylene chloride (5/95) followed by methanol saturated with ammonia/methylene chloride (5/95). The fractions containing the expected product were combined and evaporated. The residue was triturated with a mixture of pentane/ether. The solid was filtered, washed with pentane and dried under vacuum to give 4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)cinnoline (32 mg, 38%).

Provenance & Evidence