Dabco → (Z)-3-(3-(2,6-bis(trifluoromethyl)pyridin-4-yl)-1H-1,2,4-triazol-1-yl)-1-(3,3-difluoroazetidin-1-yl)prop-2-en-1-one

Participants

Reaction Steps

In a 3-neck 50 mL round-bottomed flask, 4-(1H-1,2,4-triazol-3-yl)-2,6-bis(trifluoromethyl)pyridine (3) (0.060 g, 1 eq.) and (Z)-1-(3,3-difluoroazetidin-1-yl)-3-iodoprop-2-en-1-one (0.064 g, 1.1 eq) was dissolved in DMF (2 mL). DABCO (0.047 g, 2 eq.) was added at RT. Reaction mixture was stirred for 1 h at RT. Reaction completion was monitored on TLC using MeOH:dichloromethane (0.25:9.75) as mobile phase. The reaction mixture was quenched into the ice-water slurry (50 mL) and was extracted with ethyl acetate (3×25 mL). Organic layer was washed with brine solution (3×25 mL). The organic layer was dried using anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide the 0.70 g crude compound which was purified by preparative TLC using 2.5% methanol in dichloromethane as mobile phase to afford 0.011 g (12%) title compound.

Provenance & Evidence