HCID 15099566, compound → HCID 15099591, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2,2-Dibromoethenyl)-2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenylpyridine (2.677 gm, 5.63 mmol) in dry THF (25 ml) was cooled to -78° C. and treated with n-BuLi (1.6M in hexane, 7.75 ml, 12.4 mmol) over a 1 minute period. After stirring at -78° C. for one hours, the deep green solution was quenched with saturated NH4Cl, warmed to room temperature, diluted with H2O, and extracted once with Et2O. The Et2O extract was washed with brine, dried (Na2SO4), filtered and stripped to give a yellow solid. The solid was recrystallized from a minimum amount of hot hexane to afford analytically pure 3-Ethynyl-2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenylpyridine as yellow crystals (1.572 gm, 89%).

Provenance & Evidence