(Trifluoromethyl)trimethylsilane → HCID 67545637, compound

HRID 2096797Notes

Reaction equation

HRID 2096797 reaction equation
O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:22][C:23]([Si](C)(C)C)([F:25])[F:24].[Br:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([CH3:52])[C:38]([C:40]2[CH:51]=[CH:50][C:43]3[N:44]([CH3:49])[C:45](=[O:48])[N:46]([CH3:47])[C:42]=3[CH:41]=2)=[O:39])=[C:33]([Cl:53])[CH:32]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O.CO>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([CH3:52])[C:38]([C:40]2[CH:51]=[CH:50][C:43]3[N:44]([CH3:49])[C:45](=[O:48])[N:46]([CH3:47])[C:42]=3[CH:41]=2)([OH:39])[C:23]([F:25])([F:24])[F:22])=[C:33]([Cl:53])[CH:32]=1

Participants

8

Reactant 4

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 66697339HCID 66697339, compound

Product 1

HCID 67545637HCID 67545637, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Tetrabutylammonium fluoride trihydrate (31 mg) was added to a solution of (trifluoromethyl)trimethylsilane (1 ml of a 2M solution in THF) and 5-[2-(4-bromo-2-chloro-phenyl)-propionyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (410 mg) in THF (20 ml) at room temperature. The mixture was stirred for 30 min at room temperature. MeOH (1 ml) and 1M tetrabutylammonium fluoride in THF (1 ml) were added and the mixture was stirred 1 h at room temperature. Water (50 ml) was added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane) to give the title compound (400 mg) as a colorless oil. MS (m/e)=479.0 [M+H+].

Workup

  1. stirringthe mixture was stirred 1 h at room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-8aaf55a1a70343da9b9549281f925000
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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