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

Participants

Reaction Steps

1H-Pyrrolo[2,3-b]pyridin-5-amine (20 mg, 0.150 mmol) in N,N-dimethylformamide (1.5 mL) was sequentially treated with 2-chloro-6-fluoro-3-(propylsulfonamido)benzoic acid (48.9 mg, 0.165 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (31.7 mg, 0.165 mmol), and 1-hydroxybenzotriazole (22.3 mg, 0.165 mmol) at ambient temperature. After 24 hours, the reaction mixture was diluted with ethyl acetate and washed with water (4×), sodium bicarbonate (2×), and brine (1×), dried over sodium sulfate and concentrated. The crude product was triturated with dichloromethane to provide 2-chloro-6-fluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (61.7 mg, 0.0382 mmol, 25.4% yield) as a solid. 1H NMR (400 MHz, CD3OD) δ 8.40-8.35 (d, 2H), 7.73-7.67 (q, 1H), 7.45-7.42 (d, 1H), 7.31-7.25 (t, 1H), 6.53-6.50 (d, 1H), 3.15-3.08 (t, 2H), 1.93-1.82 (m, 2H), 1.08-1.02 (t, 3H); MS (APCI-neg) m/z=409.1 (M-H).

Provenance & Evidence