Pyridine → 4-([1,1'-Biphenyl]-4-yl([1,1':3',1''-terphenyl]-4'-yl)amino)phenyl trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

N-([1,1′-biphenyl]-4-yl)-N-(4-methoxyphenyl)-[1,1′:3′,1″-terphenyl]-4′-amine (12.4 g, 24.7 mmol) and pyridine hydrochloride (28.8 g, 250.0 mmol) were purged with nitrogen for overnight. The mixture was refluxed for 2 h. After cooling, the precipitate was filtered and washed by excess water. The solid dissolved in DCM was filtered through a silica pad and washed with DCM. The solvent was removed in vacuo. The residue was dissolved in DCM (100 mL) and cooled down to 0° C. After that, pyridine (8.1 mL, 100.0 mmol) and trifluoromethanesulfonic anhydride (8.4 mL, 50.0 mmol) were added at 0° C. The mixture was stirred for 17 h from 0° C. to room temperature. The reaction mixture was quenched by the addition of saturated K2CO3 solution and extracted with DCM. The extracts were dried over MgSO4 and the solvent was removed in vacuo and the residue was purified by flash chromatography using 15% toluene/hexane (containing 0.5% triethylamine) to afford 4-([1,1′-biphenyl]-4-yl([1,1′:3′,1″-terphenyl]-4′-yl)amino)phenyl trifluoromethanesulfonate (14.5 g, 95% yield) as a white solid.

Provenance & Evidence