Pyridine → HCID 86762386, compound

HRID 1021173Notes

Reaction equation

HRID 1021173 reaction equation
[C:1]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:6]=[CH:5][C:4]([N:7]([C:26]2[CH:31]=[CH:30][C:29](OC)=[CH:28][CH:27]=2)[C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:11]=[CH:10][C:9]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:3][CH:2]=1.Cl.N1C=CC=CC=1.N1C=CC=CC=1.[F:53][C:54]([F:67])([F:66])[S:55]([O:58]S(C(F)(F)F)(=O)=O)(=[O:57])=[O:56]>>[F:53][C:54]([F:67])([F:66])[S:55]([O:58][C:29]1[CH:28]=[CH:27][C:26]([N:7]([C:4]2[CH:3]=[CH:2][C:1]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:6][CH:5]=2)[C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:11]=[CH:10][C:9]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:31][CH:30]=1)(=[O:57])=[O:56]

Participants

5

Reactant 4

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 10176127Pyridinium chlorideHCID 86762385HCID 86762385, compound

Product 1

HCID 86762386HCID 86762386, compoundYield 72%

Conditions

Temperature
0 °C

Procedure

N-([1,1′-biphenyl]-4-yl)-N-(4-methoxyphenyl)-[1,1′:3′,1″-terphenyl]-2′-amine (13.6 g, 27.0 mmol) and pyridine hydrochloride (31.1 g, 270.0 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 (8.7 mL, 108.0 mmol) and trifluoromethanesulfonic anhydride (9.1 mL, 54.0 mmol) were added at 0 0° C. The mixture was stirred for 14 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. The residue was purified by re-crystallization in 20% toluene/heptane to afford 4-([1,1′-biphenyl]-4-yl([1,1′:3′,1″-terphenyl]-2′-yl)amino)phenyl trifluoromethanesulfonate (12.0 g, 72% yield over 2 steps) as a white solid.

Workup

  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 re-crystallization in 20% toluene/heptane

Sources & evidence

ORD record
ord-0bf3500626c5492bade205f3a2996af2
Source dataset
uspto-grants-2014_05
Patent number
US08716484B1

Reaction notes

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