反应详情

A mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine (200 mg, 0.38 mmol) and tetrabutylammonium fluoride in tetrahydrofuran (1 M, 7.6 mL, 7.6 mmol) was stirred for 12 h at room temperature. The mixture was poured into brine (15 mL), extracted with ethyl acetate (2×50 mL), washed with a saturated aqueous ammonium chloride solution (3×20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to give 2-[(E)-2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine (147 mg, 100%) as a solid which was used in the next step without purification: LC/MS m/e calcd for C21H21FN2O2S [M+H]+ 385.48, observed 385.2; 1H NMR (400 MHz, MeOD) δ ppm 8.04 (d, J=8.3 Hz, 3H), 7.51-7.56 (m, 3H), 6.45 (d, J=10.1 Hz, 1H), 5.77 (s, 1H), 3.32 (br. s., 1H), 3.16-3.20 (m, 3H), 2.37-2.44 (m, 1H), 1.72-1.82 (m, 4H), 1.45-1.57 (m, 4H).

1. extractionextracted with ethyl acetate (2×50 mL)
2. washwashed with a saturated aqueous ammonium chloride solution (3×20 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated in vacuo