反应详情

4-Fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3.0 g, 10.258 mmol) was placed in THF (15 mL) at −78° C. s-BuLi (16.12 mL, 22.57 mmol) was then added dropwise and stirred for 30 minutes. Hexachloroethane (6.07 g, 25.6 mmol) in THF (10 mL) was then added rapidly, and the reaction was stirred for an additional 30 minutes. The reaction was quenched with saturated aqueous NH4Cl and extracted into hexanes. The combined organic fractions were dried, filtered and concentrated to give the crude product that was purified by column chromatography (hexanes) to give 5-chloro-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (2.1 g, 62% yield).

1. additionwas then added dropwise
2. stirringthe reaction was stirred for an additional 30 minutes
3. customThe reaction was quenched with saturated aqueous NH4Cl
4. extractionextracted into hexanes
5. customThe combined organic fractions were dried
6. filtrationfiltered
7. concentrationconcentrated
8. customto give the crude product that
9. customwas purified by column chromatography (hexanes)