反应详情

To a solution of 6-(3-nitrophenoxy)imidazo[1,2-a]pyridin-2-amine (1.40 g, 5.18 mmol) in pyridine (6 mL) was added with stirring under ice-cooling cyclopropanecarbonyl chloride (706 μL, 7.77 mmol), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was dissolved in methanol (50 mL). Sodium carbonate (1.00 g) and water (5 mL) were added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and 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 (622 mg, 35%) as a white solid.

1. stirringthe mixture was stirred at room temperature for 3 hr
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with water and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltrated
6. concentrationThe filtrate was concentrated under reduced pressure
7. dissolutionthe residue was dissolved in methanol (50 mL)
8. additionSodium carbonate (1.00 g) and water (5 mL) were added
9. stirringthe mixture was stirred at 60° C. for 2 hr
10. additionThe reaction mixture was diluted with water
11. extractionextracted with ethyl acetate
12. washThe organic layer was washed with water and 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)