反应详情

温度

0 °C

To a solution of 2-{2-cyclopentyl-1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 90, 680 mg, 1.6 mmol) in dichloromethane (20 mL) at 0° C. was added a solution of boron tribromide (0.76 ml, 8.0 mmol) in dichloromethane (10 ml). The mixture was stirred at 0° C. for 1 h. The reaction was quenched with a saturated aqueous sodium bicarbonate solution (20 mL). The mixture was extracted with dichloromethane (2×50 mL), washed with a saturated aqueous sodium bicarbonate solution (3×20 mL) and brine (3×20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification 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) afforded (2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethanol (600 mg, 94%): LC/MS m/e calcd for C22H26N2O3S [M+H]+ 399.53, observed 399.1; 1H NMR (400 MHz, CD3OD) δ ppm 8.09 (d, J=4.0 Hz, 1H), 7.85-7.93 (m, 2H), 7.61 (d, J=8.1 Hz, 2H), 7.06 (dd, J=7.7, 4.9 Hz, 1H), 6.41 (s, 1H), 4.33 (t, J=7.8 Hz, 1H), 3.85 (t, J=6.2 Hz, 2H), 3.35-3.46 (m, 2H), 2.26-2.34 (m, 1H), 2.04-2.21 (m, 1H), 1.60-1.88 (m, 4H), 1.44-1.57 (m, 2H), 1.18-1.35 (m, 3H).

1. customThe reaction was quenched with a saturated aqueous sodium bicarbonate solution (20 mL)
2. extractionThe mixture was extracted with dichloromethane (2×50 mL)
3. washwashed with a saturated aqueous sodium bicarbonate solution (3×20 mL) and brine (3×20 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated in vacuo
6. customPurification