Dimethylformamide → 4-(2,5-difluoro-4-nitrophenoxy)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

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A 100 mL flask was charged with 1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-ol (1.00 g, 3.71 mmol obtained from Example 5, step B), 1,2,4-trifluoro-5-nitrobenzene (1.32 g, 7.43 mmol), potassium carbonate (1.03 g, 7.43 mmol), and DMF (25 mL). The solution was allowed to stir overnight at room temperature for 3 days. The crude material was isolated by filtration and flash chromatography (EtOAc/Hexane 1:3) to afford 2.50 g (55%) of the desired product. LRMS M+1 (426.9) observed.

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