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

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.

1. temperatureThe mixture was refluxed for 2 h
2. temperatureAfter cooling
3. filtrationthe precipitate was filtered
4. washwashed by excess water
5. dissolutionThe solid dissolved in DCM
6. filtrationwas filtered through a silica pad
7. washwashed with DCM
8. customThe solvent was removed in vacuo
9. dissolutionThe residue was dissolved in DCM (100 mL)
10. customThe reaction mixture was quenched by the addition of saturated K2CO3 solution
11. extractionextracted with DCM
12. dry with materialThe extracts were dried over MgSO4
13. customthe solvent was removed in vacuo
14. customthe residue was purified by flash chromatography

ORDレコード

ord-7c8d8b6062f74406964f25c0c1d8c0cc

出典データセット

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08716484B1