1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(Cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)cyclobutane-1-carbonitrile

Participants

Reaction Steps

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.73 g, 0.00890 mol) in acetonitrile (22.2 mL) was added 3-(cyanomethylene)cyclobutanecarbonitrile (1.05 g, 0.00889 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (0.666 mL, 0.00445 mol). The resulting mixture was stirred at room temperature overnight, then evaporated to dryness. The mixture was purified on silica gel, eluting with 0 to 80% EtOAc in hexanes, to give the desired product as racemic mixture (320 mg, 11.5%). LCMS (M+H) 313.4.

Provenance & Evidence