1-Hydroxybenzotriazole → 2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-nitrobenzamide

Participants

Reaction Steps

3-Methoxy-1H-pyrazolo[3,4-b]pyridin-5-amine (563 mg, 3.43 mmol) in N,N-dimethylformamide (17.1 mL) was sequentially treated with 2,6-difluoro-3-nitrobenzoic acid (766.2 mg, 3.772 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (723.2 mg, 3.772 mmol), and 1-hydroxybenzotriazole (509.7 mg, 3.772 mmol) at ambient temperature. After 24 hours, the reaction 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 triturated with dichloromethane to provide 2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-nitrobenzamide (820.6 mg, 2.350 mmol, 68.5% yield) as a solid. MS (APCI-neg) m/z=347.8 (M−H).

Provenance & Evidence