3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol → 3-(5-Amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol

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Reaction Steps

To a solution of 3-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol (6 g, 15 mmol) in methanol (250 mL) was added palladium on carbon (1 g, 10%), then the reaction mixture was stirred at room temperature under hydrogen (45 psi) for 3 hours. The catalyst was filtered off, and the organic solution was concentrated under reduce pressure to give 4.6 g (83%) of 3-(5-Amino-1-benzene sulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanol. 1H NMR (400 MHz, CDCl3) δ: 8.12-8.05 (s, 1H), 7.74 (s, 1H), 7.52-7.32 (m, 5H), 6.64-6.53 (m, 1H), 4.43-4.40 (s, 1H), 4.30-4.29 (m, 1H), 2.94-2.84 (m, 3H), 2.02-1.90 (m, 1H), 1.90-1.73 (m, 6H).

Provenance & Evidence