Water → HCID 60202493, compound

Participants

Reaction Conditions

Reaction Steps

To a round-bottomed flask under argon atmosphere was added 2-chloro-6-phenyl-N-(pyridin-3-yl)quinoline-4-carboxamide (0.100 g) in 1,4-dioxane (3 ml), and the vessel was purged with argon under stirring for 5 minutes. After 5 minutes, a 2N solution of potassium carbonate in water (11 eq) was added and the flask was purged with argon under stirring for 5 minutes. (5-methylfuran-2-yl)boronic acid (1.5 eq) was then added and the tube was purged with argon under stirring for 15 minutes. Finally, palladium(0)tetrakis triphenylphosphine (0.05 eq) was added under argon and the flask was affixed to a reflux condenser and heated to 90° C. for 5 hours. The completion of the reaction was monitored on TLC using ethyl acetate:hexanes as a mobile phase. After completion of the reaction, 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 then solvent was distilled out and the crude was subjected to purification by silica gel column chromatography to provide 0.01 g of 2-(5-methylfuran-2-yl)-6-phenyl-N-(pyridin-3-yl)quinoline-4-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.12 (s, 1H), 8.97 (s, 1H), 8.41 (m, 1H), 8.39 (s, 1H), 8.30 (m, 1H), 8.19 (m, 3H), 7.78 (m, 2H), 7.55 (m, 2H), 7.48 (m, 1H), 7.44 (m, 2H), 6.43 (broad s, 1H), 2.48 (s, 3H); m/z 406.2 (MH+).

Provenance & Evidence