[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[N:8]([CH2:11][CH2:12][OH:13])[N:9]=[CH:10][C:3]=12.[H-].[Na+].[CH3:16]I>C1COCC1>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[N:8]([CH2:11][CH2:12][O:13][CH3:16])[N:9]=[CH:10][C:3]=12A solution of 675 mg of 2-(4-bromo-pyrazolo[3,4-c]pyridin-1-yl)-ethanol (Intermediate 2.2; 2.79 mmol, 1 eq.) in 33 mL THF was treated at rt with 183 mg sodium hydride (55-60% suspension; 4.18 mmol, 1.5 eq.) and stirred for 30 min upon which 0.194 mL methyl iodide (3.07 mmol, 1.1 eq.) were added and stirring was continued for 2 h. The reaction mixture was quenched with water, extracted with ethyl acetate, the combined organic layers were dried and concentrated in vacuo. Flash column chromatography provided 500 mg of the corresponding methyl ether target compound (1.95 mmol, 70% yield).
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