Cesium carbonate → (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 (150 mg, 0.48 mmol), (prepared as described for the starting material in Example 11), 5-hydroxy-2-methylindole (84 mg, 0.57 mmol) and cesium carbonate (200 mg, 0.72 mmol) in DMF (6 ml) was heated at 95° C. for 2 hours. After cooling, the mixture was filtered and the filtrate was evaporated under vacuum. The residue was purified by column chromatography eluting with methylene chloride, followed by ethyl acetate, followed by methanol/methylene chloride (1/9) followed by methylene chloride/methanol saturated with ammonia (9/1 followed by 85/15) to give 6-cyano-((2-methylindol-5-yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinoline (112 mg, 46%).

Provenance & Evidence