反应详情

A mixture of 2-[2-{[(4-methylphenyl)sulfonyl]amino}-5-(3-nitrophenoxy)pyridin-1(2H)-yl]acetamide (4.70 g, 10.6 mmol), trifluoroacetic anhydride (30 mL) and dichloromethane (40 mL) was stirred at room temperature for 5 hr. The reaction solution was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, 8N aqueous sodium hydroxide solution (10 mL) and ethanol (30 mL) were added to the residue and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, ethyl acetate) to give the title compound (1.40 g, 49%) as a white solid.

1. concentrationThe reaction solution was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
2. additionwas added to the residue
3. extractionthe mixture was extracted with ethyl acetate (×3)
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltrated
7. concentrationThe filtrate was concentrated under reduced pressure, 8N aqueous sodium hydroxide solution (10 mL) and ethanol (30 mL)
8. additionwere added to the residue
9. stirringthe mixture was stirred at room temperature for 15 hr
10. additionThe reaction mixture was diluted with water
11. extractionextracted with ethyl acetate (×3)
12. washThe organic layer was washed with saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationfiltrated
15. concentrationThe filtrate was concentrated under reduced pressure
16. customthe residue was purified by column chromatography (silica gel, ethyl acetate)