3-Fluorophenol → tert-butyl 4-(5-(3-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

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A solution of tert-butyl 4-(5-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.100 g, 0.182 mmol, see Example 13), Cu(I)Cl (0.00901 g, 0.0910 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (0.00950 mL, 0.0455 mmol), Cs2CO3 (0.119 g, 0.364 mmol) and 3-fluorophenol (0.165 mL, 1.82 mmol) in NMP (2 mL) was stirred at 106° C. for 20 hours. The reaction was then cooled to room temperature, and H2O (5 mL) was added. The reaction mixture was then extracted with ethyl acetate (15 mL), washed with brine, and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by column chromatography (hexane:ethyl acetate, 2.5:1) to give tert-butyl 4-(5-(3-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.020 g, 21%) as a solid. MS APCI (+) m/z 534.4 detected.

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