反应详情

温度

80 °C

To a solution of 2-chloro-5-nitropyridine (1.41 g, 8.92 mmol) and 3-(1-cyano-1-methylethyl)-N-(5-hydroxy-2-methylphenyl)benzamide (2.5 g, 8.5 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (1.85 g, 13.3 mmol), and the mixture was stirred at 80° C. for 18 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 (200 mL), and washed with water (200 mL). The aqueous layer was extracted with ethyl acetate (100 mL), and the combined organic layer was washed with water (200 mL) and saturated brine (200 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30→20/80). The obtained solution was concentrated under reduced pressure to give the title compound (2.68 g, 76%) as a yellow amorphous substance.

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 (200 mL)
5. washwashed with water (200 mL)
6. extractionThe aqueous layer was extracted with ethyl acetate (100 mL)
7. washthe combined organic layer was washed with water (200 mL) and saturated brine (200 mL)
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationThe insoluble material was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure
11. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30→20/80)
12. concentrationThe obtained solution was concentrated under reduced pressure