4-Iodobiphenyl → N-([1,1'-biphenyl]-4-yl)-[1,1':3',1''-terphenyl]-4'-amine

HRID 1021170Notes

Reaction equation

HRID 1021170 reaction equation
C1(P(C2CCCCC2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:19](OC)=[CH:18][CH:17]=[CH:16][C:15]=2OC)CCCCC1.[C:30]1([C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[C:38]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.IC1C=CC(C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:14]1([C:9]2[CH:8]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:17]([NH:42][C:39]2[CH:40]=[CH:41][C:36]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:37][C:38]=2[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 153224-IodobiphenylHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 123166382,4-DiphenylanilineHCID 23676156Sodium t-butoxide

Product 1

HCID 86762383N-([1,1'-biphenyl]-4-yl)-[1,1':3',1''-terphenyl]-4'-amineYield 840.5%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Xylene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.8 g, 4.4 mmol) and Pd2(dba)3 (1.0 g, 1.1 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′:3′,1″-terphenyl]-4′-amine (9.8 g, 40.0 mmol), 4-iodobiphenyl (10.3 g, 36.7 mmol), sodium tert-butoxide (7.0 g, 73.4 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 13 h. After cooling, the reaction mixture was filtered through a silica pad and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash chromatography using 40-60% toluene/hexane to afford N-([1,1′-biphenyl]-4-yl)-[1,1′:3′,1″-terphenyl]-4′-amine (14.7 g, 92% yield) as a white solid.

Workup

  1. customXylene (250 mL) was bubbled with nitrogen for 15 min
  2. customThe mixture was bubbled with nitrogen for 15 min
  3. customThe mixture was bubbled with nitrogen for 15 min
  4. temperaturerefluxed for 13 h
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered through a silica pad
  7. washwashed with toluene
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7e5407e0152849ab8e1f57f1f6b24da6
Source dataset
uspto-grants-2014_05
Patent number
US08716484B1

Reaction notes

Loading…