4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester → 4-(5-Amino-1-benzenesulfonyl 1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Palladium hydroxide (20% wt on carbon, 2.2 g) was added to a solution of 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (22.0 g, 43.9 mmol) in acetic acid (220 mL) under nitrogen. The reaction was evacuated and purged with hydrogen and the reaction warmed to 50° C. for 8 hours. The reaction vessel was recharged with hydrogen gas and stirred at room temperature for 18 hours. The mixture was then filtered through Celite® and the filtrate concentrated to dryness under vacuum. The resulting residue was partitioned between DCM and sodium hydrogen carbonate (sat. aq.), the organic layer dried with sodium sulphate and concentrated under vacuum. The residues were triturated with methanol, filtered, washed with diethyl ether and air dried to afford 16.9 g (82%) of 4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester. 1H NMR (400 MHz, CDCl3) δ: 8.14 (dd, 2H), 7.85 (s, 1H), 7.54 (m, 1H), 7.49 (d, 1H), 7.45 (m, 2H), 6.52 (d, 1H), 4.80 (br s, 1H), 4.05 (s, 2H), 3.86 (m, 1H), 2.97 (t, 2H), 2.61 (m, 2H), 2.03 (d, 2H), 1.46 (s, 9H).

Provenance & Evidence