2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → HCID 70654424, compound

HRID 539489Notes

Reaction equation

HRID 539489 reaction equation
CC(C)([O-])C.[Na+].[C:7]1([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:21]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:22]=[CH:23][N:24]=3)[CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[C:32]1[CH:33]=[C:34]([C:38]2[N:39]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH:40]=[CH:41][N:42]=2)[CH:35]=[CH:36][CH:37]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1>[C:7]1([N:13]([C:36]2[CH:37]=[CH:32][CH:33]=[C:34]([C:38]3[N:39]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:40]=[CH:41][N:42]=3)[CH:35]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:21]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:22]=[CH:23][N:24]=3)[CH:15]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 706543692-(3-bromophenyl)-1-phenyl-1H-imidazoleHCID 70654544HCID 70654544, compound

Product 1

HCID 70654424HCID 70654424, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium tert-butoxide (1.082 g, 11.27 mmol), N-phenyl-3-(1-phenyl-1H-imidazol-2-yl)aniline (2.45 g, 7.87 mmol), 2-(3-bromophenyl)-1-phenyl-1H-imidazole (2.1 g, 7.04 mmol), tris(dibenzylideneacetone)palladium(0) (Pd2dba3) (0.161 g, 0.176 mmol) and 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (0.289 g, 0.704 mmol) were charged into the reaction vessel with 100 mL of toluene. This mixture was degassed with nitrogen then was heated to reflux for 24 h. The reaction mixture was cooled to room temperature then was partitioned with 100 mL of water. The toluene layer was separated and the aqueous was extracted with another 100 mL of toluene. The toluene extracts were combined, dried over magnesium sulfate then were filtered and stripped under vacuum. The crude residue was passed through a silica gel column (15-30% acetone/DCM) and was purified if necessary using neutral alumina chromatography (7-10% ethyl acetate/DCM) yielding N-phenyl-3-(1-phenyl-1H-imidazol-2-yl)-N-(3-(1-phenyl-1H-imidazol-2-yl)phenyl)aniline (1.35 g, 2.55 mmol, 36.2%).

Workup

  1. customThis mixture was degassed with nitrogen
  2. temperaturethen was heated
  3. temperatureto reflux for 24 h
  4. customthen was partitioned with 100 mL of water
  5. customThe toluene layer was separated
  6. extractionthe aqueous was extracted with another 100 mL of toluene
  7. dry with materialdried over magnesium sulfate
  8. filtrationthen were filtered
  9. customwas purified if necessary using neutral alumina chromatography (7-10% ethyl acetate/DCM)

Sources & evidence

ORD record
ord-1900359997c944d0967b129ab2ed5555
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

Loading…