Sodium Carbonate → 1-[4-(9,10-diphenylanthracen-2-yl)phenyl]-2-phenyl-1H-benzimidazole

HRID 1172775Notes

Reaction equation

HRID 1172775 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.[C:23]1([C:29]2[C:30]3[C:35]([C:36]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[C:37]4[C:42]=2[CH:41]=[C:40](B(O)O)[CH:39]=[CH:38]4)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[C:23]1([C:29]2[C:30]3[C:35]([C:36]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[C:37]4[C:42]=2[CH:41]=[C:40]([C:2]2[CH:3]=[CH:4][C:5]([N:8]5[C:12]6[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=6[N:10]=[C:9]5[C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)=[CH:6][CH:7]=2)[CH:39]=[CH:38]4)=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 230940711-(4-Bromophenyl)-2-phenyl-1H-benzimidazoleHCID 231602159,10-Diphenylanthracene-2-boronic Acid

Product 1

HCID 589538151-[4-(9,10-diphenylanthracen-2-yl)phenyl]-2-phenyl-1H-benzimidazoleYield 92.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.0 g (2.9 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 1.2 g (3.2 mmol) of 9,10-diphenylanthracene-2-boronic acid, and 0.067 g (0.058 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 20 mL of 1,2-dimethoxyethane. Then, 10 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 1.6 g of a greenish white solid (90% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 598 with respect to a molecular weight of 598.24.

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 8 hours in an argon atmosphere
  3. customAfter the completion of the reaction
  4. filtrationthe resultant was filtered
  5. washthe resultant solid was washed with water, methanol, and toluene

Sources & evidence

ORD record
ord-814ada64fb4847f18afe8b2ec7b2dc3e
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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