A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (1.01 g, 3.00 mmol), 1-benzyl-2-methyl-piperidin-4-ylamine (674 mg, 3.30 mmol) and diisopropylethylamine (1.83 mL, 10.5 mmol) in propan-2-ol (30 mL) was heated to reflux for 1 hour. The mixture was filtered through Celite® and the filtrate concentrated under vacuum. Purification by column chromatography on silica gel (gradient: 0 to 30% ethyl acetate in toluene) afforded 990 mg (65%) of racemic cis (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(1-benzyl-2-methyl-piperidin-4-yl)-amine as a yellow foam and 320 mg (21%) of racemic trans (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(1-benzyl-2-methyl-piperidin-4-yl)-amine as a yellow foam. Analysis for racemic cis: LCMS (Method I, ESI): RT=2.53 min, m+H=506.4; 1H NMR (400 MHz, CDCl3) δ: 9.09 (s, 1H), 8.98 (d, 1H), 8.19 (dd, 2H), 7.61 (m, 2H), 7.54-7.49 (m, 2H), 7.35 (br s, 4H), 7.17 (m, 1H), 6.67 (s, 1H), 4.18 (br s, 1H), 3.94 (br s, 1H), 3.18 (br s, 1H), 2.97 (br s, 1H), 2.36 (s, 1H), 2.21-1.98 (m, 5H), 1.41-1.20 (m, 3H). Analysis for racemic trans: LCMS (Method I, ESI): RT=2.56 min, m+H=506.4; 1H NMR (400 MHz, DMSO) δ: 9.07 (d, 1H), 8.92 (s, 1H), 8.15-8.10 (m, 2H), 7.80 (m, 2H), 7.66 (t, 2H), 7.38-7.19 (m, 4H), 7.02 (d, 1H), 4.42 (s, 1H), 3.89 (d, 1H), 2.80-2.57 (m, 2H), 2.34-2.24 (m, 1H), 1.93-1.58 (m, 4H), 1.15 (d, 3H).
