3-[4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-propionitrile → 3-[4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-propionitrile

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-[4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-propionitrile (19.3 g, 4.25 mmol) and palladium on carbon (3.7 g, 10%, wet, Degussa, E101 NE/W) in EtOAc (150 ml) was stirred under a hydrogen atmosphere (2-3 balloons) at 50° C. for 24 h. The reaction mixture was cooled to 25° C. then was filtered through Celite and the Celite 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 6% CH3OH in CH2Cl2) afforded 3-[4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-propionitrile (13.6 g, 75%) as a grey foam. 1H NMR (400 MHz, CDCl3) δ 8.17-8.09 (m, 2H), 7.83 (s, 1H), 7.54 (t, J=7.4 Hz, 1H), 7.49-7.41 (m, 3H), 6.52 (d, J=4.2 Hz, 1H), 4.76 (d, J=8.4 Hz, 1H), 3.79-3.66 (m, 1H), 2.94-2.82 (m, 3H), 2.72 (t, J=6.9 Hz, 2H), 2.51 (t, J=6.9 Hz, 2H), 2.29 (td, J=11.5, 2.1 Hz, 2H), 2.12-2.00 (m, 2H), 1.58 (qd, J=10.9, 3.6 Hz, 2H). This material was used in the next step below without additional characterization.

Provenance & Evidence