(Trifluoromethyl)trimethylsilane → 4-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxy}-benzonitrile

HRID 1095903Notes

Reaction equation

HRID 1095903 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:30][C:31]1[CH:32]=[C:33]([CH:43]=[CH:44][C:45]=1[CH:46]([CH3:56])[C:47]([C:49]1[CH:54]=[CH:53][N:52]=[C:51]([CH3:55])[CH:50]=1)=[O:48])[O:34][C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=1>C1COCC1>[Cl:30][C:31]1[CH:32]=[C:33]([CH:43]=[CH:44][C:45]=1[CH:46]([CH3:56])[C:47]([OH:48])([C:49]1[CH:54]=[CH:53][N:52]=[C:51]([CH3:55])[CH:50]=1)[C:2]([F:4])([F:3])[F:1])[O:34][C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 666990324-{3-Chloro-4-[1-methyl-2-(2-methyl-pyridin-4-yl)-2-oxo-ethyl]-phenoxy}-benzonitrile

Product 1

HCID 666991754-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(2-methyl-pyridin-4-yl)-propyl]-phenoxy}-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 2M solution of (trifluoromethyl)trimethylsilane in THF (0.23 ml) and a 0.1M solution of tetrabutylammonium fluoride trihydrate in THF (0.42 ml) were added to 4-{3-chloro-4-[1-methyl-2-(2-methyl-pyridin-4-yl)-2-oxo-ethyl]-phenoxy}-benzonitrile (80 mg) in THF (1 ml). The mixture was stirred for 1 h at room temperature and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:1) to give the title compound (60 mg) as a light yellow solid. MS (m/e)=447.1 [M+H+].

Workup

  1. concentrationconcentrated to an oil
  2. customThe residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:1)

Sources & evidence

ORD record
ord-b7d81d5aa879485cb92467f7c820b288
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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