反应详情

温度

80 °C

To a solution of 2-chloro-5-nitropyridine (1.06 g, 6.68 mmol) and N-(4-cyano-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide (2.0 g, 6.55 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (1.35 g, 9.82 mmol), and the mixture was stirred at 80° C. for 20 hr. The reaction mixture was cooled to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL), washed with water (150 mL) and saturated brine (150 mL×2), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→40/60), and further purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100). The obtained solution was concentrated under reduced pressure to give the title compound (0.68 g, 24%) as a pale-yellow oil.

1. temperatureThe reaction mixture was cooled to room temperature
2. filtrationthe insoluble material was filtered off
3. concentrationthe filtrate was concentrated under reduced pressure
4. additionThe obtained residue was diluted with ethyl acetate (300 mL)
5. washwashed with water (150 mL) and saturated brine (150 mL×2)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationThe insoluble material was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→40/60)
10. customfurther purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
11. concentrationThe obtained solution was concentrated under reduced pressure