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

A mixture of 4-[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-but-1-enyl]-2-fluoro-benzoic acid methyl ester (2.50 g, 5 mmol) and tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 50 mL) was stirred at 25° C. for 40 h. The reaction was quenched with a saturated aqueous ammonium chloride solution (50 mL). The mixture was extracted with ethyl acetate (2×150 mL), washed with a saturated aqueous ammonium chloride solution (3×100 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)-3-methyl-but-1-enyl]-benzoic acid methyl ester (660 mg, 36%) which was used in the next step without further purification: LC/MS m/e calcd for C20H18F2N2O2 [M+H]+ 357.38, observed 356.9.

1. customThe reaction was quenched with a saturated aqueous ammonium chloride solution (50 mL)
2. extractionThe mixture was extracted with ethyl acetate (2×150 mL)
3. washwashed with a saturated aqueous ammonium chloride solution (3×100 mL), brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated in vacuo

ORD 기록

ord-e2fbd0b4301f430b82bdd40b17173285

출처 데이터셋

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08222416B2