HCID 46238383, compound → HCID 49790728, compound

Participants

Reaction Conditions

Reaction Steps

To a sealed tube under argon atmosphere was added 6-bromo-2-(furan-2-yl)-N-(pyridin-3-yl)quinoline-4-carboxamide (0.250 g) in DMF (5 ml), and the vessel was purged with argon under stirring for 5 minutes. After 5 minutes, 2N solution of sodium carbonate in water (3.3 ml) was added and the tube was purged with argon under stirring for 5 minutes. Phenylboronic acid (0.115 g) was then added and the tube was purged with argon under stirring for 15 minutes. Finally, palladium(0)tetrakis triphenylphosphine (0.034 g) was added under argon and the tube was sealed and heated to 90° C. for 16 hours. The completion of the reaction was monitored by TLC using ethyl acetate:hexanes (5:5) as a mobile phase. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (100 ml) and then washed with water (5*100 ml). The ethyl acetate layer was dried over anhydrous sodium sulphate, and the solvent was removed by distillation and the crude product was subjected to purification by silica gel column chromatography, eluting with 1-2% methanol in methylene chloride to provide 0.154 g of 2-(furan-2-yl)-6-phenyl-N-(pyridin-3-yl)quinoline-4-carboxamide (1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.13 (s, 1H), 8.59 (m, 1H), 8.39 (m, 1H), 8.37 (s, 1H), 8.30 (m, 1H), 8.25 (s, 1H), 8.19 (m, 2H), 8.02 (s, 1H), 7.79 (m, 2H), 7.55 (m, 3H), 7.46 (m, 2H), 6.79 (m, 1H); m/z 392.2 (MH+).

Provenance & Evidence