1,3-Propanediol → 1-Phenyl-7-(4-pyridyl)-5-trifluoromethylbenzimidazole

HRID 644530Notes

Reaction equation

HRID 644530 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.[N:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(O)CCO.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.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>[C:11]1([N:8]2[C:7]3[C:2]([C:24]4[CH:25]=[CH:26][N:21]=[CH:22][CH:23]=4)=[CH:3][C:4]([C:17]([F:20])([F:19])[F:18])=[CH:5][C:6]=3[N:10]=[CH:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 112099651-Phenyl-7-(4-pyridyl)-5-trifluoromethylbenzimidazole

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (3.0 g, 7.5 mmol), pyridine 4-boronic acid (1.38 g, 11.2 mmol), 1,3-propanediol (2.7 ml, 37.3 mmol), potassium carbonate (5.2 g, 37.3 mmol) and bis(triphenylphosphin)palladium dichloride (200 mg, 0.28 mmol) in a mixture of dimethoxyethane (30 ml) and water (15 ml) was stirred at reflux for 5 days. The cooled reaction mixture was concentrated under reduced pressure, and the concentrate was partitioned between water and ethyl acetate. The organic phase was dried and concentrated under reduced pressure, and the concentrate was purified by column chromatography on silica gel eluting with a mixture of ligroin and ethyl acetate (1:1 v/v). The product was isolated as a yellowish solid by evaporation of solvent from the eluate (1.55 g, 61%) m/z, 340.1 (M+H)+.

Workup

  1. temperatureat reflux for 5 days
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customthe concentrate was partitioned between water and ethyl acetate
  5. customThe organic phase was dried
  6. concentrationconcentrated under reduced pressure
  7. customthe concentrate was purified by column chromatography on silica gel eluting with a mixture of ligroin and ethyl acetate (1:1 v/v)
  8. customThe product was isolated as a yellowish solid by evaporation of solvent from the eluate (1.55 g, 61%) m/z, 340.1 (M+H)+

Sources & evidence

ORD record
ord-50c58617b5e141fcb663f8f867085a07
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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