1,3-Propanediol → 7-(3-Chlorophenyl)-1-Phenyl-5-trifluoromethylbenzimidazole

HRID 644503Notes

Reaction equation

HRID 644503 reaction equation
I[C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[Cl:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C(O)CCO.C(=O)([O-])[O-].[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:21][C:22]1[CH:27]=[C:26]([C:2]2[C:7]3[N:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:9]=[N:10][C:6]=3[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=2)[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 113946817-(3-Chlorophenyl)-1-Phenyl-5-trifluoromethylbenzimidazole

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A mixture of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (1.0 g, 2.6 mmol), 3-chlorobenzeneboronic acid (0.6 g, 3.87 mmol), 1,3-propanediol (1 ml, 12.9 mmol), potassium carbonate (1.8 g, 12.9 mmol) and bis(triphenylphosphin)palladium dichloride (100 mg, 0.14 mmol) was stirred at reflux for one hour. The cooled mixture was partitioned between water and ethyl acetate. The organic extract was dried and concentrated under reduced pressure. The concentrate was purified by chromatography on silica gel eluting with a mixture of ethyl acetate and ligroin (2:3, v/v). Removal of solvent left the desired product as a white solid (0.9 g, 94%) m/z, 373.1 (M+H)+.

Workup

  1. temperatureat reflux for one hour
  2. customThe cooled mixture was partitioned between water and ethyl acetate
  3. extractionThe organic extract
  4. customwas dried
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was purified by chromatography on silica gel eluting with a mixture of ethyl acetate and ligroin (2:3
  7. customRemoval of solvent
  8. waitleft the desired product as a white solid (0.9 g, 94%) m/z, 373.1 (M+H)+

Sources & evidence

ORD record
ord-099283daa5f04f1db5c2756dcf89991e
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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