Tetrabutylammonium Fluoride → 5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-benzenesulfonyl-5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine (900 mg, 1.8 mmol) and tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 4 ml) was stirred at 25° C. for 20 h. The reaction was quenched with a saturated aqueous ammonium chloride solution (30 mL). The mixture was extracted with ethyl acetate (2×50 mL), washed with a saturated aqueous ammonium chloride solution (3×25 mL), brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 5-fluoro-2-[1-(4-methanesulfonyl-phenyl)-3-methyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine (600 mg, 92%): LC/MS m/e calcd for C19H19FN2O2S [M+H]+ 359.44, observed 358.8.

Provenance & Evidence