3-Methylpyridine → HCID 76315512, compound

Participants

Reaction Steps

2-Methyl-6-nitroaniline (540 mg, 3.54 mmol), 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid (1 g, 3.54 mmol), CH3CN (0.3 M, 11.8 mL) and 3-picoline (0.69 mL, 7.08 mmol, 2.0 eq) were introduced to a 50 mL round flask and subjected to a reaction at room temperature. After 10 minutes, the reaction mixture thus obtained was added with methylsulfonylchloride (0.41 mL, 5.31 mmol, 1.5 eq.), subjected to a reaction at 30° C. for 24 hours, and followed by a further reaction at 40° C. for 24 hours. Upon completion of the reaction, CH3CN was removed from the reaction mixture under reduced pressure, and the residue was extracted with 1 M HCl (20 mL) and ethyl acetate (20 mL), and, then, extracted with NaHCO3 (20 mL) and ethyl acetate (20 mL), washed with brine (20 mL). The organic layer thus obtained was dried over MgSO4 and concentrated under reduced pressure. Subsequently, the residue was purified by silica gel column chromatography (MC:EA=9:1) to obtain the title compound (1.27 g, yield: 82%).

Provenance & Evidence