Tetrabutylammonium Fluoride → 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

5-Bromo-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyri dine (12.60 g, 33.9 mmol) was placed in THF (200 mL) at 0° C. TBAF (33.9 mL, 1M THF solution) was then added, and the reaction was then stirred for 1 hour at 0° C. The reaction was quenched with NaHCO3 (aq.) and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:5 DCM:MeOH) to give 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine (6.8 g, 93.2% yield).

Provenance & Evidence