反应详情

To a stirred solution of 6-chloro-5-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine (1.276 g, 6.91 mmol) and 2-pyridine methanol (0.800 mL, 8.29 mmol) in dimethyl sulphoxide (10 mL), under a nitrogen atmosphere, is added 60% sodium hydride (0.332 g, 8.29 mmol) portionwise, and reaction stirred at room temperature overnight. The reaction is then heated to 80° C. for 1 h, cooled to room temperature and further 60% sodium hydride (0.090 g, 2.32 mmol) added. After 30 minutes of stirring at room temperature, the reaction is further heated at 80° C. for 30 minutes. The reaction is cooled, poured onto brine (ca. 50 mL) and the product extracted with CHCl3 (ca. 2×30 mL). The combined organic extracts are dried over magnesium sulphate, filtered, and concentrated in vacuo to give a brown oil. This is purified by column chromatography on silica, eluting with 0 to 80% EtOAc in hexane, to give the title compound as a light green oil (1.445 g, 5.62 mmol). MS (m/z): 258 (M+1).

1. customreaction
2. temperatureThe reaction is then heated to 80° C. for 1 h
3. temperaturecooled to room temperature
4. stirringAfter 30 minutes of stirring at room temperature
5. temperaturethe reaction is further heated at 80° C. for 30 minutes
6. temperatureThe reaction is cooled
7. additionpoured onto brine (ca. 50 mL)
8. extractionthe product extracted with CHCl3 (ca. 2×30 mL)
9. dry with materialThe combined organic extracts are dried over magnesium sulphate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customto give a brown oil
13. customThis is purified by column chromatography on silica
14. washeluting with 0 to 80% EtOAc in hexane