反应详情

温度

50 °C

A suspension of 3-[4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-butyronitrile (11.3 g, 24.1 mmol) and palladium on carbon (3.2 g, 10%, wet, Degussa, E101 NE/W) in EtOAc (150 ml) was stirred under a hydrogen atmosphere (2-3 balloons) at 50° C. for 14 h. The reaction mixture was cooled to 25° C. then was filtered through Celite and the Celite was washed with EtOAc (2×20 ml). The filtrate and washings were concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (gradient: 0 to 8% CH3OH in CH2Cl2) afforded 3-[4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-butyronitrile (6.51 g, 61%) as a grey foam. TLC: 5% CH3OH in CH2Cl2, Rf=0.40; 1H NMR (400 MHz, CDCl3) δ 8.12 (d, J=7.8 Hz, 2H), 7.81 (s, 1H), 7.56-7.49 (m, 1H), 7.48-7.39 (m, 3H), 6.52 (d, J=4.2 Hz, 1H), 4.74 (d, J=8.5 Hz, 1H), 3.75-3.63 (m, 1H), 3.13-3.00 (m, 1H), 2.90-2.69 (m, 3H), 2.51 (dd, J=16.7, 6.3 Hz, 1H), 2.45-2.32 (m, 3H), 2.06 (d, J=10.9 Hz, 2H), 1.61-1.46 (m, 2H), 1.19 (d, J=6.7 Hz, 3H).

1. temperatureThe reaction mixture was cooled to 25° C.
2. filtrationthen was filtered through Celite
3. washthe Celite was washed with EtOAc (2×20 ml)
4. concentrationThe filtrate and washings were concentrated under reduced pressure
5. customPurification of the residue by column chromatography on silica gel (gradient: 0 to 8% CH3OH in CH2Cl2)