Acetohydroxamic Acid → 7-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amine

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3-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)-2-fluorobenzonitrile 15 (90 mg, 0.299 mmol) was added to a mixture of acetohydroxamic acid, CH3C(O)NHOH (0.0675 g, 0.899 mmol) and potassium carbonate (0.145 g, 1.049 mmol) in 4 mL dimethylformamide and the resultant reaction mixture was heated for 2 hours at 50° C. The solvent was removed, diluted with ethyl acetate and washed with saturated sodium bicarbonate (1×20 mL) followed by brine (1×20 mL), dried over anhydrous sodium sulfate, concentrated and purified by a Biotage purification system eluting with ethyl acetate and hexanes to obtain 17 (35 mg, 40%).

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