Sodium Carbonate → 1h-Benzo[d]imidazole,5-(4-chlorophenyl)-1,2-diphenyl-

HRID 1172771Notes

Reaction equation

HRID 1172771 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.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=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>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:17]=[CH:16][C:5]3[N:6]([C:15]4[CH:16]=[CH:17][CH:2]=[CH:3][CH:4]=4)[C:7]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[N:8][C:4]=3[CH:3]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 230940805-Bromo-1-methyl-2-phenyl-1H-benzo[d]imidazole

Product 1

HCID 231602311h-Benzo[d]imidazole,5-(4-chlorophenyl)-1,2-diphenyl-Yield 145.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2.0 g (7.2 mmol) of 5-bromo-1-methyl-2-phenyl-1H-benzimidazole, 1.2 g (7.9 mmol) of 4-chlorophenylboronic acid, and 0.17 g (0.14 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 resultant had been stood to cool, an aqueous layer was removed and an organic layer was dried with magnesium sulfate. After the solvent had been distilled off under reduced pressure, the resultant solid was purified by means of silica gel column chromatography to obtain 2.0 g of 5-(4-chlorophenyl)-1,2-diphenyl-1H-benzimidazole (87% yield).

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 8 hours in an argon atmosphere
  3. temperatureto cool
  4. customan aqueous layer was removed
  5. dry with materialan organic layer was dried with magnesium sulfate
  6. distillationAfter the solvent had been distilled off under reduced pressure
  7. customthe resultant solid was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-90ff416a5f484d2abe26ef00fa066f79
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

Loading…