反应详情

温度

50 °C

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 116, 147 mg, 0.38 mmol) and 10% palladium on activated carbon (0.2 g) in methanol (50 mL) was heated at 50° C. under hydrogen (50 psi) for 5 h. After cooling to room temperature, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo. The residue was purified using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine as a white solid (60 mg, 41%): LC/MS m/e calcd for C21H23FN2O2S [M+H]+ 387.49, observed 387.2; 1H NMR (400 MHz, CD3OD) δ ppm 8.00 (t, J=2.3 Hz, 1H), 7.90 (d, J=8.3 Hz, 2H), 7.58-7.66 (m, 3H), 6.40 (s, 1H), 4.31 (t, J=8.0 Hz, 1H), 3.09 (s, 3H), 2.24-2.32 (m, 1H), 2.08-2.16 (m, 1H), 1.60-1.87 (m, 5H), 1.45-1.56 (m, 2H), 1.18-1.30 (m, 2H).

1. temperatureAfter cooling to room temperature
2. customthe catalyst was removed by filtration
3. washwashed with ethyl acetate
4. concentrationThe filtrate was concentrated in vacuo
5. customThe residue was purified