反应详情

tert-Butyl 2,5-dichloro-4-fluorobenzoate (Preparation 218, 251 mg, 0.61 mmol) was added to a solution of 5-chloro-6-cyclopropylpyridin-3-ol (Preparation 69, 161 mg, 0.61 mmol) and potassium carbonate (393 mg, 1.82 mmol) in dimethylsulfoxide (5 mL). The reaction mixture was stirred at room temperature for 18 hours then diluted with sodium hydroxide (1M, 5 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with heptane:dichloromethane (from 95:5 to 60:40) to afford the title compound as a colourless oil (116 mg, 30%).

1. extractionextracted with ethyl acetate (3×15 mL)
2. dry with materialThe combined organic layers were dried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude compound was purified by silica gel column chromatography
6. washeluting with heptane