反应详情

温度

160 °C

6-Ethoxy-1H-indol-5-ol described in Production Example 15-4 (7.0 g, 39.5 mmol) was dissolved in dimethylsulfoxide (40 mL) under nitrogen atmosphere, then N-(4-chloropyridin-2-yl)acetamide described in Production Example 1-5 (8.09 g, 47.4 mmol) and potassium tert-butoxide (4.88 g, 43.5 mmol) were added at room temperature, and the mixture was heated and stirred at 160° C. for 4 hours. The reaction liquid was cooled to room temperature and water and ethyl acetate were added for partition. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with water twice and then with a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under vacuum. The residue was dissolved in dichloromethane, and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=3:1-2:1-3:2-1:3-1:4-0:1), and then the target fraction was concentrated under vacuum to obtain the title compound (7.16 g, 58%).

1. additionwere added at room temperature
2. temperaturethe mixture was heated
3. customThe reaction liquid
4. temperaturewas cooled to room temperature
5. customfor partition
6. extractionThe aqueous layer was extracted with ethyl acetate
7. washthe combined organic layer was washed with water twice
8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated under vacuum
11. dissolutionThe residue was dissolved in dichloromethane
12. customthe resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=3:1-2:1-3:2-1:3-1:4-0:1)
13. concentrationthe target fraction was concentrated under vacuum