Sodium Carbonate → HCID 67507790, compound

Participants

Reaction Conditions

Reaction Steps

A dry flask containing 4-amino-5-iodo-2-morpholinobenzonitrile (140 mg, 0.42 mmol) in dry DMF (3.0 mL) was cooled to 0° C., then sodium hydride, 60% dispersion in mineral oil (34.7 mg, 0.87 mmol) was added carefully in portions. The mixture was stirred at 0° C. for 15 minutes, then 4-chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (185 mg, 0.64 mmol) was added in portions. Upon complete addition, the mixture was warmed to 60° C. After 2.5 h, the reaction was cooled to rt then was carefully treated with 10% sodium carbonate solution. The black mixture was subsequently extracted five times with DCM:methanol (90:10). The organic extraction was then washed one time with brine and dried over anhydrous magnesium sulfate. After filtration and concentration, the black residue was treated with methanol and placed on the rotovap. (without vac.) in a 45° C. water bath. After 30 minutes, the solid was filtered and rinsed twice with methanol to afford an off white solid as 4-(5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ylamino)-5-iodo-2-morpholinobenzonitrile. Mass Spectrum (pos.) m/e: 583.9 (M+H)+.

Provenance & Evidence