3-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-ylmethyl]-pyridine

Synthesis

69966-55-8

269410-08-4

864754-21-2

The general procedure for the synthesis of 1-(3-pyridinylmethyl)-1H-pyrazole-4-boronic acid pinacol ester from 3-bromomethylpyridine and 4-pyrazole boronic acid pinacol ester was as follows: 3-bromomethylpyridine (2.67 g, 15.5 mmol) and 4-pyrazole boronic acid pinacol ester (3.01 g, 15.5 mmol) were dissolved in N,N-dimethylformamide (DMF, 20 mL). ) in N,N-dimethylformamide (DMF, 20 mL), followed by addition of potassium carbonate (2.2 g, 16 mmol) to the reaction system. The reaction mixture was heated to 80 °C and the reaction was stirred at this temperature for 8 hours. After completion of the reaction, the mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL x 3), the organic phases were combined and washed with saturated brine (20 mL) and dried over anhydrous sodium sulfate. After the solvent was removed by concentration under reduced pressure, the residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate, v/v=1/1.5) to give 280 mg of the target product in the form of light yellow oil in 6.33% yield.

References