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

HRID 1172776Notes

Reaction equation

HRID 1172776 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.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]1[C:34]2[C:39]([C:40]([C:50]3[CH:59]=[CH:58][C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[CH:51]=3)=[C:41]3[C:46]=1[CH:45]=[C:44](B(O)O)[CH:43]=[CH:42]3)=[CH:38][CH:37]=[CH:36][CH:35]=2.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>[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]1[C:34]2[C:39]([C:40]([C:50]3[CH:59]=[CH:58][C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[CH:51]=3)=[C:41]3[C:46]=1[CH:45]=[C:44]([C:2]1[CH:3]=[CH:4][C:5]([N:8]4[C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=5[N:10]=[C:9]4[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:6][CH:7]=1)[CH:43]=[CH:42]3)=[CH:38][CH:37]=[CH:36][CH:35]=2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 230940711-(4-Bromophenyl)-2-phenyl-1H-benzimidazoleHCID 23160220[9,10-Di(naphthalen-2-yl)anthracen-2-yl]boronic acid

Product 1

HCID 231602351-[4-[9,10-di(2-naphtyl)anthracen-2-yl]phenyl]-2-phenyl-1H-benzimidazoleYield 84%

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, 1.5 g (3.2 mmol) of 9,10-di(2-naphtyl)anthracene-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 1.7 g of a greenish white solid (84% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 698 with respect to a molecular weight of 698.27.

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-a9662bc92d79432f84fec3cddf915d34
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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