Tetrabutylammonium Fluoride → 5-Fluoro-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

Tetrabutylamonium fluoride, 1M in THF (2 mL), was added to a stirred solution of 5-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1 g, 3.94 mmol) in THF (10 mL) at room temperature and stirred for 15 min. The solvent was evaporated and the crude product was purified by Biotage HPFC system (40-75% EtOAc/Hexane) to afford 5-fluoro-1H-pyrrolo[2,3-b]pyridine as a white solid (0.45 g, 84); Mass Spec.; MS 137 (M+1); 1H NMR(DMSO-d6, 500 MHz) δ 11.75(s, 1H), 8.17(t,1H), 7.81(dd,1H), 7.55(t,1H), 6.44(dd,1H).

Provenance & Evidence