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

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Reaction Steps

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (750 mg, 2.20 mmol), 4-amino-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (525 mg, 2.50 mmol) and diisopropylethylamine (1.36 mL, 7.80 mmol) in propan-2-ol (30 mL) was heated to reflux for 65 hours. The cooled reaction mixture was filtered and the yellow solid further purified by column chromatography on silica gel (gradient: 0 to 30% ethyl acetate in cyclohexane) to afford 910 mg (79%) of 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester. LCMS (Method H, ESI): RT=4.35 min, m+H=516.2; 1H NMR (400 MHz, DMSO) δ: 9.42 (s, 1H), 8.95 (s, 1H), 8.15 (dd, 2H), 7.84-7.76 (m, 2H), 7.66 (m, 2H), 7.06 (d, 1H), 3.57 (m, 2H), 3.23-3.08 (m, 1H), 2.09 (d, 2H), 1.80 (m, 2H), 1.57 (s, 3H), 1.39 (s, 9H).

Provenance & Evidence