Diisopropylethylamine → racemic cis (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(1-benzyl-4-methyl-piperidin-3-yl)-amine

Participants

Reaction Steps

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (692 mg, 2.10 mmol), racemic cis 1-benzyl-4-methyl-piperidin-3-ylamine (460 mg, 2.30 mmol) and diisopropylethylamine (1.25 mL, 7.20 mmol) in propan-2-ol (30 mL) was heated to reflux for 2 hours. The cooled reaction mixture was filtered and the yellow solid dried under vacuum to afford 940 mg (90%) of racemic cis (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(1-benzyl-4-methyl-piperidin-3-yl)-amine. LCMS (Method H, ESI): RT=2.61 min, m+H=506.2; 1H NMR (400 MHz, DMSO) δ: 9.67 (d, 1H), 8.94 (s, 1H), 8.13 (dd, 2H), 7.75 (m, 2H), 7.66 (m, 2H), 7.30-7.10 (m, 6H), 4.54 (d, 1H), 3.49 (m, 2H) 2.83 (t, 2H), 2.27 (d, 1H), 2.07 (m, 1H), 1.91 (br s, 1H), 1.47 (m, 2H), 0.81 (d, 3H).

Provenance & Evidence