3-Aminopyridine → HCID 46238383, compound

Participants

Reaction Steps

To a 250 ml three necked round bottom flask equipped with thermo pocket under argon atmosphere was added 6-bromo-2-(furan-2-yl)quinoline-4-carboxylic acid (5 g) in DMF (15 ml). The solution was stirred for 5 minutes. After 5 minutes, EDAC.HCl (N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride) (3.6 g), HOBT (2.54 g) and DMAP (3.83 g) were added at RT and the reaction mixture was stirred at room temperature for 0.5 h. 3-amino pyridine (1.6 g) was then added in one lot and the reaction was allowed to stir at RT for 12 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 then solvent was distilled out and the crude was subjected to purification by silica gel column chromatography, eluting with 1.5% methanol in methylene chloride to provide 6-bromo-2-(furan-2-yl)-N-(pyridin-3-yl)quinoline-4-carboxamide (2.0 g).

Provenance & Evidence