Water → 1-(2-(pyrrolidin-1-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

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Reaction Steps

To a suspension of sodium hydride (0.272 g, 11.34 mmol) in N,N-dimethylformamide (13 mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 5.15 mmol) and 2-chloroethylpyrrolidine HCl salt (0.964 g, 5.67 mmol) as solutions in N,N-dimethylformamide (2 mL each). The reaction was stirred at room temperature for 0.5 hours and then heated to 65° C. for 3 hours. The reaction was cooled to room temperature and diluted with ethyl acetate (50 mL). Water (50 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 292.2 [M+H]+;

Provenance & Evidence