HCID 21471327, compound → HCID 11066164, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2,2-dibromoethenyl)-2-(4-fluorophenyl)-4-(1-methylethyl)quinoline (2.563 gm, 5.71 mmol) in dry THF (30 ml) was cooled to -78° C. and treated with n-BuLi (1.5M in hexane, 8.0 ml, 12 mmol) over a 5 minute period. After stirring at -78° C. for 1.25 hours, the brown solution was quenched with saturated NH4Cl, warmed to room temperature, diluted with H2O, and extracted 2× with Et2 O. The combined Et2O extracts were washed with brine, dried (Na2SO4), filtered and stripped to give a yellow solid. The solid was recrystallized from hot hexane to afford analytically pure 3-ethynyl-2-(4-fluorophenyl)-4-(1-methylethyl)quinoline as off-white crystals (1.205 gm, 73%).

Provenance & Evidence