Ammonium Chloride → 6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehyde

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Reaction Steps

6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide (1.0 g) was dissolved in THF (25 mL). At 0° C. methylmagnesium bromide solution (1 M, 3.9 mL) was added slowly, the mixture was warmed to r.t. while stirring overnight. Saturated ammonium chloride solution was added, the mixture was extracted with dichloromethane, the organic phases were dried over magnesium sulfate and concentrated in a membrane pump vacuum. The residue was purified by fish chromatography (silica, heptane/ethyl acetate gradient) giving 1-[6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone (1.0 g, quantitative yield with impurities).

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