Potassium Carbonate → 7-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-1,6-naphthyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To 3-[4,6-dibromo-2-(2-chloro-4-fluorophenyl)pyridin-3-yl]-N-(2,6-dichlorophenyl)propanamide (3.14 g, 5.40 mmol) in DMF (50 mL) was added K2CO3 (1.49 g, 10.8 mmol) and CuI (1.54 g, 10.8 mmol). The resulting reaction mixture was evacuated and purged with argon 3 times, and then heated at 155° C. (oil bath) for 35 min. The reaction mixture was cooled to rt and diluted with 240 mL of half-saturated aqueous NaHCO3 and 120 mL of ethyl acetate. The layers were separated and the aqueous layer was extracted with 2×180 mL of ethyl acetate. The combined organic layers were washed with 120 mL of brine, dried over Na2SO4, and concentrated under reduced pressure. The product was purified by flash chromatography on 2 Biotage 40M columns, eluting with 50:50 hexanes-CH2Cl2 to yield 7-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-1,6-naphthyridin-2(1H)-one. Mass spectrum (ESI) 499.2 (M+1).

Provenance & Evidence