Sodium Carbonate → HCID 59631176, compound

Participants

Reaction Conditions

Reaction Steps

A dry flask containing 5-bromo-5′-fluoro-2′-methoxy-2,4′-bipyridin-3-amine (54.1 mg, 0.18 mmol) in dry DMF (3 mL) was cooled to 0° C., then sodium hydride, 60% dispersion in mineral oil (22.1 mg, 0.55 mmol) was added carefully in portions. The mixture was stirred at 0° C. for 15 min, then 4-chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (55.7 mg, 0.19 mmol) was added in portions. Upon complete addition, the mixture was warmed to 70° C. After 18 h, the reaction was cooled to rt then was carefully treated with 10% sodium carbonate solution. The black mixture was subsequently extracted 5 times with DCM:MeOH (90:10). The organic extraction was then washed one time with brine and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on basic alumina (0-35% EtOAc in hexanes) to afford a yellow residue as N-(5-bromo-5′-fluoro-2′-methoxy-2,4′-bipyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine that was used without further purification.

Provenance & Evidence