Ethyl Acetate → (1-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1H-pyrazol-3-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

In a sealed tube, a suspension of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-pyrazole (100.0 mg, 0.5154 mmol), tert-butyl-(2-iodoethoxy)-dimethylsilane (196 mg, 0.685 mmol), and Cs2CO3 (271 mg, 0.832 mmol) in DMF (3 mL) was stirred at 100° C. for 16 h. The sample was suspended between EtOAc and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, giving the title material as the boronic acid, as a yellow oil (203.4 mg). MS (ES+): m/z 270.18/271.13/272.15 (19/79/15) [MH+]. HPLC: tR=3.33 min (CAD, ZQ3, polar—5 min).

Provenance & Evidence