Water → 1-(Pyridin-2-ylmethyl)-1H-pyrazole-4-boronic acid, pinacol ester

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Reaction Steps

To a suspension of sodium hydride (0.096 ml, 5.15 mmol) in N,N-dimethylformamide (8.59 ml) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.5 g, 2.58 mmol). After 0.5 hours, 2-chloromethylpyridine hydrochloride salt (0.423 g, 2.58 mmol), and tetrabutylammonium iodide (0.095 g, 0.258 mmol) were added as solution in N,N-dimethylformamide (2 mL). The reaction was cooled to room temperature and diluted with ethyl acetate (10 mL). Water (10 mL) was added, and the layers were separated. The aqueous layer was extracted with additional ethyl acetate (2×30 mL). The combined organics were washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification. MS ESI(+) m/z 285.9 [M+H]+.

Provenance & Evidence