Dimethyl Sulfate → 7-(2,4-dichloro-phenyl)-2-methyl-2H-pyrazolo[3,4-c]pyridine

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A mixture of 7-(2,4-dichloro-phenyl)-1H-pyrazolo[3,4-c]pyridine (31; 0.107 g; 0.405 mmol), 4 mL of THF, and 60% sodium hydride/mineral oil (0.020 g, 0.50 mmol sodium hydride) was stirred for 3 h. To the green solution was added dimethyl sulfate (0.040 mL, 0.42 mmol). The resulting yellow, cloudy solution was stirred for 30 m, then quenched with silica gel and concentrated. Column chromatography (0→50% EtOAc/hexanes) afforded of 7-(2,4-dichloro-phenyl)-2-methyl-2H-pyrazolo[3,4-c]pyridine as a white solid (32; 0.029 g; 26%).

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