1-Hydroxybenzotriazole → 2,6-dichloro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

1H-Pyrrolo[2,3-b]pyridin-5-amine (192 mg, 1.44 mmol) in N,N-dimethylformamide (7.2 mL) was sequentially treated with 2,6-dichloro-3-(propylsulfonamido)benzoic acid (690.5 mg, 2.212 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (466.4 mg, 2.433 mmol), and 1-hydroxybenzotriazole (328.8 mg, 2.433 mmol) and heated to 60° C. After 24 hours, the reaction mixture was allowed to cool to ambient temperature. The mixture was diluted with ethyl acetate, washed with water (4×), sodium bicarbonate (2×), and brine (1×), dried over sodium sulfate, and concentrated. The crude product was applied directly to a silica gel column and eluted with a gradient (30% to 100%) of ethyl acetate-hexanes to provide 2,6-dichloro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (10.5 mg, 0.0246 mmol, 3.41% yield) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 11.70-11.59 (s, 1H), 10.77-10.68 (s, 1H), 9.88-9.75 (s, 1H), 8.39-8.30 (m, 2H), 7.56-7.47 (m, 3H), 6.49-6.45 (d, 1H), 3.21-3.04 (m, 2H), 1.82-1.70 (m, 2H), 1.03-0.95 (t, 3H); MS (APCI-neg) m/z=425.1 (M-H).

Provenance & Evidence