Sodium Carbonate → 5-(9,10-diphenylanthracen-2-yl)-1-methyl-2-phenyl-1H-benzimidazole

HRID 1172781Notes

Reaction equation

HRID 1172781 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH3:15])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[C:18]1([C:24]2[C:25]3[C:30]([C:31]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[C:32]4[C:37]=2[CH:36]=[C:35](B(O)O)[CH:34]=[CH:33]4)=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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:18]1([C:24]2[C:37]3[C:32]([C:31]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)=[C:30]4[C:25]=2[CH:26]=[C:27]([C:2]2[CH:17]=[CH:16][C:5]5[N:6]([CH3:15])[C:7]([C:9]6[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=6)=[N:8][C:4]=5[CH:3]=2)[CH:28]=[CH:29]4)=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 230940805-Bromo-1-methyl-2-phenyl-1H-benzo[d]imidazoleHCID 231602159,10-Diphenylanthracene-2-boronic Acid

Product 1

HCID 231602395-(9,10-diphenylanthracen-2-yl)-1-methyl-2-phenyl-1H-benzimidazoleYield 76.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.4 g (4.9 mmol) of 5-bromo-1-methyl-2-phenyl-1H-benzimidazole, 2.0 g (5.3 mmol) of 9,10-diphenylanthracene-2-boronic acid, and 0.11 g (0.097 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 2.0 g of a greenish white solid (76% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 536 with respect to a molecular weight of 536.23.

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-daf2e9649f8041b78829971139a7fdef
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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