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

HRID 539479
Notes
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Reaction equation

HRID 539479 reaction equation
[C:1]1([C:11]2[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=2)[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.Br[C:25]1[CH:26]=[C:27]([C:31]2[N:32]([C:36]3[C:41]([CH:42]([CH3:44])[CH3:43])=[CH:40][CH:39]=[CH:38][C:37]=3[CH:45]([CH3:47])[CH3:46])[CH:33]=[CH:34][N:35]=2)[CH:28]=[CH:29][CH:30]=1.CC(C)([O-])C.[Na+].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:45]([C:37]1[CH:38]=[CH:39][CH:40]=[C:41]([CH:42]([CH3:44])[CH3:43])[C:36]=1[N:32]1[CH:33]=[CH:34][N:35]=[C:31]1[C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[N:14]([C:13]1[CH:21]=[CH:22][CH:23]=[C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][N:2]=2)[CH:12]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:47])[CH3:46]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 706542932-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazoleHCID 706542973-(isoquinolin-1-yl)-N-phenylaniline

Product 1

HCID 706546753-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-(3-(isoquinolin-1-yl)phenyl)-N-phenylaniline
Yield 78%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

3-(isoquinolin-1-yl)-N-phenylaniline (1.65 g, 5.57 mmol), 2-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole (2.256 g, 5.89 mmol), sodium tert-butoxide (0.802 g, 8.35 mmol), Pd2dba3 (0.102 g, 0.111 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (0.184 g, 0.449 mmol) were charged into the reaction vessel with 150 mL of toluene. This mixture was evacuated and back-filled with nitrogen. The reaction mixture was then heated to reflux for 18 h. The reaction mixture was cooled to room temperature then was diluted with 75 mL of water. This mixture was then filtered through a pad of Celite®. The toluene layer was separated and dried over magnesium sulfate. The organics were filtered and stripped under vacuum. The crude residue was passed through a silica gel column using 2-40% ethyl acetate/DCM yielding 3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-N-(3-(isoquinolin-1-yl)phenyl)-N-phenylaniline (2.60 g, 4.34 mmol, 78% yield).

Workup

  1. customThis mixture was evacuated
  2. additionback-filled with nitrogen
  3. temperatureThe reaction mixture was then heated
  4. temperatureto reflux for 18 h
  5. additionthen was diluted with 75 mL of water
  6. filtrationThis mixture was then filtered through a pad of Celite®
  7. customThe toluene layer was separated
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe organics were filtered

Sources & evidence

ORD record
ord-804cc5cd3e8e4596a3b283c067834141
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871361B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes