2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → 3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-phenyl-N-(3-(quinolin-2-yl)phenyl)aniline

HRID 539476Notes

Reaction equation

HRID 539476 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].Br[C:31]1[CH:32]=[C:33]([C:37]2[N:38]([C:42]3[C:47]([CH:48]([CH3:50])[CH3:49])=[CH:46][CH:45]=[CH:44][C:43]=3[CH:51]([CH3:53])[CH3:52])[CH:39]=[CH:40][N:41]=2)[CH:34]=[CH:35][CH:36]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>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].C1(C)C=CC=CC=1>[CH:51]([C:43]1[CH:44]=[CH:45][CH:46]=[C:47]([CH:48]([CH3:50])[CH3:49])[C:42]=1[N:38]1[CH:39]=[CH:40][N:41]=[C:37]1[C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH:9]=1)([CH3:53])[CH3:52]

Participants

7

Reactant 4

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 706542932-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazoleHCID 70654371N-phenyl-3-(quinolin-2-yl)aniline

Product 1

HCID 706544313-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-phenyl-N-(3-(quinolin-2-yl)phenyl)anilineYield 91%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

N-phenyl-3-(quinolin-2-yl)aniline (3 g, 10.12 mmol), sodium tert-butoxide (1.555 g, 16.20 mmol), 2-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole (4.07 g, 10.63 mmol), Pd2dba3 (0.232 g, 0.253 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (0.415 g, 1.012 mmol) were charged into the reaction vessel with 250 mL of toluene. This mixture was evacuated and back-filled with nitrogen. The reaction mixture was then heated at reflux for 20 h. The reaction mixture was cooled to room temperature then was diluted with 200 mL of water. The toluene layer was separated and the aqueous was extracted with 100 mL of toluene. The organic extracts were combined and removed under vacuum. The crude residue was passed through a silica gel column using 5-25% ethyl acetate/DCM yielding 3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-phenyl-N-(3-(quinolin-2-yl)phenyl)aniline (5.5 g, 91% yield) as a yellow foamy solid.

Workup

  1. customThis mixture was evacuated
  2. additionback-filled with nitrogen
  3. temperatureThe reaction mixture was then heated
  4. temperatureat reflux for 20 h
  5. additionthen was diluted with 200 mL of water
  6. customThe toluene layer was separated
  7. extractionthe aqueous was extracted with 100 mL of toluene
  8. customremoved under vacuum

Sources & evidence

ORD record
ord-fa67088951e04d3ab1e025af93337d3f
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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