反应详情

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (3.39 mL) was added to a solution of (4-{[tert-butyl(dimethyl)silyl]oxy}-3-chlorophenyl)(5-chloro-6-methoxypyridin-2-yl)methanone (700 mg) in tetrahydrofuran (10 mL) at room temperature, and the mixture was stirred at room temperature for two hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (10 mL), and 2-iodopropane (333 μL) and potassium carbonate (464 mg) were sequentially added at room temperature, followed by stirring at 65° C. for three hours. The reaction solution was returned to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the title compound as a colorless oil (538 mg, 93%).

1. extractionfollowed by extraction with ethyl acetate
2. washThe organic layer was washed with brine
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationafter which the filtrate was concentrated under reduced pressure
6. dissolutionThe resulting residue was dissolved in N,N-dimethylformamide (10 mL)
7. addition2-iodopropane (333 μL) and potassium carbonate (464 mg) were sequentially added at room temperature
8. stirringby stirring at 65° C. for three hours
9. customwas returned to room temperature
10. additionwater was added
11. extractionfollowed by extraction with ethyl acetate
12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
13. filtrationfiltered
14. customThe solvent was then evaporated under reduced pressure
15. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)