Potassium Phosphate, Tribasic → N-(1,1':4',1''-terphenyl-3-yl)indolo[2,3-a]carbazole

HRID 64535

Reaktionsgleichung

Reaktionsgleichung von HRID 64535
[CH:1]1[C:6]2[N:7]=[C:8]3[C:20]4[C:12]([C:13]5[C:18]([N:19]=4)=[CH:17][CH:16]=[CH:15][CH:14]=5)=[CH:11][CH:10]=[C:9]3[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:22]1[CH:23]=[C:24]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:30][CH:29]=2)[CH:25]=[CH:26][CH:27]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:24]1([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:30][CH:29]=2)[CH:23]=[CH:22][CH:27]=[C:26]([N:7]2[C:8]3[C:9](=[CH:10][CH:11]=[C:12]4[C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=5[NH:19][C:20]4=3)[C:5]3[C:6]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:25]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 153297101-Bromo-3-(4-phenylphenyl)benzeneHCID 21882147Indolo[2,3-a]carbazole

Produkt 1

HCID 68089261N-(1,1':4',1''-terphenyl-3-yl)indolo[2,3-a]carbazoleAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83681Tris(1,1-dimethylethyl)phosphineKatalysatorHCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Indolo[2,3-a]carbazole (9.8 g) was dissolved in 150 ml of dry toluene under nitrogen. 12.9 g of 3-bromo-p-terphenyl, 0.65 g of tris(dibenzylideneacetone) dipalladium, 0.46 g of tri-t-butylphosphine and 40.3 g of potassium orthophosphate were added and heated to reflux for 16 h. After the completion of reaction, the reaction was quenched with water. The reaction mixture was then extracted using ethyl acetate; and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. Subsequent silica gel column chromatography using ethyl acetate/hexane (1:9) as eluent, yielded 12.6 g of N-(1,1′:4′,1″-terphenyl-3-yl)indolo[2,3-a]carbazole.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. customAfter the completion of reaction
  4. customthe reaction was quenched with water
  5. extractionThe reaction mixture was then extracted
  6. dry with materialand the organic layer was dried over anhydrous sodium sulfate
  7. customevaporated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b1a99e4574d64a38801f876484d345f0
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09450192B2

Verknüpfte Notizen

Wird geladen…