1,3-Propanediol → 7-(1-Methyl-5-indolyl)-1-phenyl-5-trifluoromethylbenzimidazole

HRID 644537Notes

Reaction equation

HRID 644537 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.[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][C:27](B(O)O)=[CH:28][CH:29]=2)[CH:24]=[CH:23]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>[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][C:27]([C:2]3[C:7]4[N:8]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[CH:9]=[N:10][C:6]=4[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=3)=[CH:28][CH:29]=2)[CH:24]=[CH:23]1

Participants

8

Reactant 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 27598671-Methyl-1H-indole-5-boronic acidHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 114179227-(1-Methyl-5-indolyl)-1-phenyl-5-trifluoromethylbenzimidazoleYield 84%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (1.0 g, 2.5 mmol), 1-methyl-5-indolyl boronic acid (0.65 g, 3.73 mmol), 1,3-propanediol (0.9 ml, 12.4 mmol), potassium carbonate (1.71 g, 12.4 mmol) and bis(triphenylphosphin)palladium dichloride (100 mg, 0.14 mmol) in a mixture of dimethoxyethane (20 ml) and water (10 ml) was stirred at reflux in a nitrogen atmosphere for 1 hour. The cooled reaction mixture was partitioned between ethyl acetate and water and the organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The residue was triturated in ethanol to afford the title product as an off-white solid (0.82 g, 84%) m/z, 392.1 (M+H)+.

Workup

  1. temperatureat reflux in a nitrogen atmosphere for 1 hour
  2. customThe cooled reaction mixture
  3. customwas partitioned between ethyl acetate and water
  4. dry with materialthe organic layer was dried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue was triturated in ethanol

Sources & evidence

ORD record
ord-99de9afd82a94fd99c78a14b26a1e6d3
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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