Cesium carbonate → 9,10-di(2-naphthyl)-2-(2-phenyl-1H-benzimidazol-1-yl)anthracene

HRID 1172782Notes

Reaction equation

HRID 1172782 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:36]1([C:42]2[NH:46][C:45]3[CH:47]=[CH:48][CH:49]=[CH:50][C:44]=3[N:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C1C2C(=CC=C3C=2N=NC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cu](I)I>[CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][C:26]=1[C:5]1[C:4]2[C:13]([C:12]([C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)=[C:11]3[C:6]=1[CH:7]=[C:8]([N:46]1[C:45]4[CH:47]=[CH:48][CH:49]=[CH:50][C:44]=4[N:43]=[C:42]1[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH:9]=[CH:10]3)=[CH:14][CH:15]=[CH:2][CH:3]=2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 128552-PhenylbenzimidazoleHCID 601987Benzo[h]cinnolineHCID 222471572-Bromo-9,10-di(naphthalen-2-yl)anthracene

Product 1

HCID 231602259,10-di(2-naphthyl)-2-(2-phenyl-1H-benzimidazol-1-yl)anthraceneYield 35.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

5.1 g (10 mmol) of 2-bromo-9,10-di(2-naphthyl)anthracene, 2.3 g (12 mmol) of 2-phenyl-1H-benzimidazole, 0.19 g (11.0 mmol) of copper iodide, and 3.6 g (2.0 mmol) of 9,10-phenanthroline were dissolved into a 2 M solution of cesium carbonate in dimethylformamide (DMF), and the whole was refluxed under heating for 48 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered. The filtrate was poured into 1 L of 10-mass % hydrochloric acid, and the whole was extracted with methylene chloride. An organic layer was taken out and dried with magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resultant solid was purified by means of silica gel column chromatography to obtain 2.2 g of a pale yellow solid (35% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 622 with respect to a molecular weight of 622.24.

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 48 hours in an argon atmosphere
  3. customAfter the completion of the reaction
  4. filtrationthe resultant was filtered
  5. additionThe filtrate was poured into 1 L of 10-mass % hydrochloric acid
  6. extractionthe whole was extracted with methylene chloride
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant solid was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-b14732359192416fbddfeac0cfd11b95
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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