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

HRID 64535
Notes
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Reaction equation

HRID 64535 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

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

Product 1

HCID 68089261N-(1,1':4',1''-terphenyl-3-yl)indolo[2,3-a]carbazoleYield 67.5%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphine
Catalyst
HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalyst
HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b1a99e4574d64a38801f876484d345f0
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09450192B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes