反应详情

To a solution of 1-cyclopropyl-6-fluoro-1H-pyrrolo[2,3-b]pyridine (2.03 g, 11.52 mmol) in DMF (38 mL) is added sodium hydroxide (0.506 g, 12.67 mmol), followed by N-bromosuccinimide (2.26 g, 12.67 mmol) portionwise over 5 minutes, resulting in an exothermic reaction (28° C.). The mixture is stirred at room temperature for 15 min., and further sodium hydroxide (46.1 mg, 1.15 mmol) and N-bromosuccinimide (0.205 g, 1.15 mmol) are added. Stirring is continued at room temperature for 30 min. Further sodium hydroxide (46.1 mg, 1.15 mmol) and N-bromosuccinimide (0.205 g, 1.15 mmol) are added. The reaction mixture is stirred at room temperature for 16 h and then poured onto brine (ca. 500 mL) and extracted with CHCl3 (ca. 2×300 mL). The organic layers are combined and dried over magnesium sulphate, filtered, and concentrated in vacuo to give a brown oil, which is purified by column chromatography on silica, eluting with 0 to 100% DCM in isohexane, to give the title compound as a white powder (2.32 g, 9.10 mmol). MS (m/z): 255/257 (M+1).

1. customresulting in an exothermic reaction (28° C.)
2. stirringStirring
3. waitis continued at room temperature for 30 min
4. stirringThe reaction mixture is stirred at room temperature for 16 h
5. additionpoured onto brine (ca. 500 mL)
6. extractionextracted with CHCl3 (ca. 2×300 mL)
7. dry with materialdried over magnesium sulphate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a brown oil, which
11. customis purified by column chromatography on silica
12. washeluting with 0 to 100% DCM in isohexane