Tetrabutylammonium Fluoride → 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 4[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-2-fluoro-benzoic acid methyl ester (400 mg, 0.74 mmol) and tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 4 ml) was stirred at 25° C. for 16 h. The reaction was quenched with a saturated aqueous ammonium chloride solution (20 mL). The mixture was extracted with ethyl acetate (2×100 mL), washed with a saturated aqueous ammonium chloride solution (3×50 mL), brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-benzoic acid methyl ester (250 mg, 84%) as a solid which was used in the next step without further purification: LC/MS m/e calcd for C22H20F2N2O3 [M+H] 399.41, observed 399.0.

Provenance & Evidence