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

HRID 539473
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 539473
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]
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Komponenten

6

Edukt 4

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

Produkt 1

HCID 706542349-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)phenyl)-9H-carbazole-2-carbonitrile
Ausbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9a71db0a0c244d2dad98a01f75604642
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08871361B2

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