HCID 67344547, compound → HCID 67342218, compound

Participants

Reaction Conditions

Reaction Steps

Zinc (24 g) was added to a solution of 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid benzyl ester (21.3 g, 40 mmol) in acetic acid (150 mL) and heated to 60° C. for 30 minutes. After cooling the mixture was filtered and the filtrate concentrated to dryness under vacuum. The resulting residue was partitioned between ethyl acetate and sodium hydrogen carbonate (sat. aq.), the organics layer dried with sodium sulphate and concentrated under vacuum. Purification by column chromatography on silica gel (gradient: 100% ethyl acetate) afforded 14.7 g (75%) of 4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid benzyl ester as a purple residue. 1H NMR (400 MHz, CDCl3) δ: 8.16-8.11 (m, 2H), 7.87 (s, 1H), 7.58-7.41 (m, 4H), 7.35 (m, 5H), 6.52 (d, 1H), 5.13 (s, 2H), 4.89 (br s, 1H), 4.11 (m, 2H), 3.95-3.84 (m, 1H), 3.10-2.96 (m, 2H), 2.10-2.05 (m, 1H), 1.54-1.40 (m, 2H).

Provenance & Evidence