Aniline → HCID 70654544, compound

HRID 539488Notes

Reaction equation

HRID 539488 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O.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:20]1([NH:19][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[N:9]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:10]=[CH:11][N:12]=3)[CH:3]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 706543692-(3-bromophenyl)-1-phenyl-1H-imidazole

Product 1

HCID 70654544HCID 70654544, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

2-(3-bromophenyl)-1-phenyl-1H-imidazole (5.7 g, 19.05 mmol), aniline (0.85 g, 9.13 mmol), sodium tert-butoxide (2.55 g, 26.6 mmol), Pd2dba3 (0.167 g, 0.183 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (0.299 g, 0.730 mmol) were charged into the reaction flask with 150 mL of m-xylenes. This mixture was heated at reflux for 1 day. The reaction mixture was diluted with 100 mL of water then was filtered through a pad of Celite®. The m-xylene 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 10-30% acetone/DCM yielding N-phenyl-3-(1-phenyl-1H-imidazol-2-yl)aniline (1.72 g, 5.5 mmol, 60.6% yield).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 1 day
  3. filtrationthen was filtered through a pad of Celite®
  4. customThe m-xylene layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe organics were filtered

Sources & evidence

ORD record
ord-6c1805fa64ec43a4967a4471eabec57e
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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