Tetrabutylammonium Fluoride → 4-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine

Participants

Reaction Steps

To a solution 4-chloro-5-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.04 g) in tetrahydrofuran (4.77 mL) was added dropwise tetra-n-butylammonium fluoride (0.372 mL, 1.0M in tetrahydrofuran) at ambient temperature. After stirred for 1 hour, the mixture was poured into brine (15 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layeres were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane/EtOAc=1/1) to give 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine (520 mg) as a colorless solid.

Provenance & Evidence