Potassium Phosphate, Tribasic → 9-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)phenyl)-9H-carbazole-2-carbonitrile

HRID 539473Notes

Reaction equation

HRID 539473 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]([C:13]3[C:18]([CH:19]([CH3:21])[CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=3[CH:22]([CH3:24])[CH3:23])[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH:25]1[C:37]2[NH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]=2[CH:28]=[CH:27][C:26]=1[C:38]#[N:39].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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]>[CH:22]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]([CH3:21])[CH3:20])[C:13]=1[N:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:4]1[CH:3]=[C:2]([N:36]2[C:37]3[CH:25]=[C:26]([C:38]#[N:39])[CH:27]=[CH:28][C:29]=3[C:30]3[C:35]2=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:7]=[CH:6][CH:5]=1)([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 117356699H-carbazole-2-carbonitrileHCID 706542932-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole

Product 1

HCID 706542349-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)phenyl)-9H-carbazole-2-carbonitrileYield 93.4%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

2-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole (4.39 g, 11.45 mmol), 9H-carbazole-2-carbonitrile (2 g, 10.40 mmol), Pd2dba3 (0.333 g, 0.364 mmol) and 2-dicyclohexylphosphino-2′,6′ dimethoxybiphenyl (S-Phos) (0.597 g, 1.457 mmol) were charged into the reaction flask with 300 mL of m-xylenes. Potassium phosphate tribasic anhydrous (3.86 g, 18.21 mmol) was ground into a fine powder using a mortar and pestle then was added to the reaction mixture. The reaction mixture was degassed with nitrogen then was heated at reflux for 5½ days. This biphasic mixture was passed through a plug of Celite® to remove some insoluble materials. The organic layer was separated and dried over magnesium sulfate. The organics were filtered and concentrated under vacuum. The crude residue was passed through a silica gel column using 25% ethyl acetate/10% DCM/hexanes. The product fractions yielded 9-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)phenyl)-9H-carbazole-2-carbonitrile (93.4% yield) as a tan solid.

Workup

  1. additionthen was added to the reaction mixture
  2. customThe reaction mixture was degassed with nitrogen
  3. temperaturethen was heated
  4. temperatureat reflux for 5½ days
  5. customto remove some insoluble materials
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe organics were filtered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9a71db0a0c244d2dad98a01f75604642
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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