3-Methylpyridine → HCID 76315512, compound

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%).

1. customsubjected to a reaction at room temperature
2. customthe reaction mixture thus obtained
3. customsubjected to a reaction at 30° C. for 24 hours
4. customfollowed by a further reaction at 40° C. for 24 hours
5. customwas removed from the reaction mixture under reduced pressure
6. extractionthe residue was extracted with 1 M HCl (20 mL) and ethyl acetate (20 mL)
7. extractionextracted with NaHCO3 (20 mL) and ethyl acetate (20 mL)
8. washwashed with brine (20 mL)
9. customThe organic layer thus obtained
10. dry with materialwas dried over MgSO4
11. concentrationconcentrated under reduced pressure
12. customSubsequently, the residue was purified by silica gel column chromatography (MC:EA=9:1)

ORD record

ord-dae214628b854cbd90071937f835c525

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018233B2