反应详情

A solution of 1-ethyl-6-fluoro-1H-pyrrolo[2,3-b]pyridine (16.38 g, 99.77 mmol) in DMF (300 mL) is cooled to 15° C. with stirring. To this is added sodium hydroxide (4.39 g, 109.7 mmol), followed by N-bromosuccinimide (19.53 g, 109.7 mmol) portionwise over 5 minutes, and then the reaction is allowed to stir at room temperature overnight. The reaction is poured onto brine (ca. 500 mL) and the product extracted with CHCl3 (ca. 2×300 mL). The combined organic phase is 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 60% DCM in hexane, to give the title compound as a light yellow oil (23.4 g, 96.4 mmol). MS (m/z): 243/245 (M+1).

1. stirringto stir at room temperature overnight
2. additionThe reaction is poured onto brine (ca. 500 mL)
3. extractionthe product extracted with CHCl3 (ca. 2×300 mL)
4. dry with materialThe combined organic phase is dried over magnesium sulphate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a brown oil
8. customThis is purified by column chromatography on silica
9. washeluting with 0 to 60% DCM in hexane