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

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Reaction Steps

A stirred mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (23.8 g, 70.5 mmol), 1-BOC-4-aminopiperidine (15.5 g, 77.5 mmol) and diisopropylethylamine (17.0 mL, 98.7 mmol) in propan-2-ol (250 mL) was heated to reflux for approximately 2 hours. After cooling, the resulting suspension was filtered and the solid washed with propan-2-ol and diethyl ether, then air dried to afford 33.6 g (95%) of 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester as a yellow solid. 1H NMR (400 MHz, CDCl3) δ: 9.12 (br d, 1H), 9.09 (s, 1H), 8.21 (m, 2H), 7.66 (m, 2H), 7.53 (t, 2H), 6.69 (d, 1H), 4.14 (m, 1H), 4.01 (d, 2H), 3.12 (t, 2H), 2.11-2.08 (m, 2H), 1.65-1.64 (m, 2H), 1.48 (s, 9H).

Provenance & Evidence