Potassium Carbonate → 6-Cyano-4-(3-methylindol-5-yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chloro-6-cyano-7-(3-(pyrrolidin-1-yl)propoxy)quinoline (200 mg, 0.63 mmol), (prepared as described for the starting material in Example 11), potassium carbonate (131 mg, 0.95 mmol) and 3-methyl-5-hydroxyindole (102.5 mg, 0.69 mmol), (Can. J. Chem. 1964, 42, 514), in DMF (6 ml) was stirred at 95° C. for 2 hours. After cooling, silica was added and the volatiles was removed under vacuum. The product was eluted with methylene chloride followed by methylene chloride/ethyl acetate (containing 20% methanol) (9/1 followed by 8/2) followed by methylene chloride/methanol (saturated with ammonia) (9/1 followed by 8/2). The fractions containing the expected product were combined and evaporated. The residue was triturated with ether, filtered and dried under vacuum to give 6-cyano-4-(3-methylindol-5-yloxy)-7-(3-(pyrrolidin-1-yl)propoxy)quinoline (151 mg, 56%).

Provenance & Evidence