Diisopropylethylamine → cis 3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4-ylamino)cyclohexanecarbonitrile

Participants

Reaction Steps

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (1.01 g, 3.00 mmol), 3-amino-cyclohexanecarbonitrile (3.30 mmol assumed) and diisopropylethylamine (2.60 mL, 15.0 mmol) in propan-2-ol (30 mL) were heated to reflux for 2 hours. The cooled reaction mixture was filtered and the yellow solid further purified by column chromatography on silica gel (gradient: 0 to 10% ethyl acetate in toluene) to afford 300 mg (23%) of cis 3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4-ylamino)cyclohexanecarbonitrile. 1H NMR (400 MHz, DMSO) δ: 8.90 (s, 1H), 8.80 (d, 1H), 8.13 (m, 2H), 7.84 (d, 1H), 7.76 (m, 1H), 7.66 (m 2H), 7.09 (d, 1H), 4.11 (m, 1H), 3.10 (m, 1H), 2.28 (m, 1H), 1.98 (m, 2H), 1.79 (m, 2H), 1.50 (m, 3H). The filtrate was concentrated and purified by column chromatography on silica gel (gradient: 0 to 10% ethyl acetate in toluene) to afford 220 mg (17%) of trans 3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4-ylamino)cyclohexanecarbonitrile. LCMS (Method I, ESI): RT=3.76 min, m+H=426.1; 1H NMR (400 MHz, DMSO) δ: 8.92 (s, 1H), 8.13 (dd, 2H), 7.88 (d, 1H), 7.77 (t, 1H), 7.65 (t, 2H), 6.99 (d, 1H), 4.27 (m, 1H), 3.26 (m, 1H), 2.18 (m, 1H), 1.99 (m, 1H), 1.91 (m, 1H), 1.83-1.58 (m, 5H).

Provenance & Evidence