Trimethylsilyl iodide → 5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-2(1H)-pyridone

HRID 963313Notes

Reaction equation

HRID 963313 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([C:20]3[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[O:22][N:21]=3)=[CH:15][C:14]=2[CH3:29])=[CH:5][N:4]=1.C[Si](I)(C)C>ClCCCl>[F:28][C:25]([F:26])([F:27])[C:23]1[O:22][N:21]=[C:20]([C:16]2[CH:15]=[C:14]([CH3:29])[C:13]([O:12][CH2:11][CH2:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3](=[O:2])[NH:4][CH:5]=3)=[C:18]([CH3:19])[CH:17]=2)[N:24]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 190820582-Methoxy-5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine

Product 1

HCID 190820095-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-2(1H)-pyridoneYield 34.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 3.0 g (7.36 mmol) of 2-methoxy-5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine and 3.6 ml (3.4 eq) of trimethylsilyl iodide in 60 ml of 1,2-dichloroethane was refluxed under nitrogen for 1 h. The above red solution was quenched with methanol, poured into water, and diluted with methylene chloride. The organic layer was washed with sodium bisulfite, dried over magnesium sulfate, and concentrated in vacuo. The residue was recrystallized from isopropyl acetate to afford 1 g (34.5%) of 5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-2(1H)-pyridone, as a white, flaky solid, m.p. 128.5°-130.5° C.

Workup

  1. customThe above red solution was quenched with methanol
  2. additionpoured into water
  3. additiondiluted with methylene chloride
  4. washThe organic layer was washed with sodium bisulfite
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from isopropyl acetate

Sources & evidence

ORD record
ord-9d70c68476814bec9ae7d6ea49d6235d
Source dataset
uspto-grants-1998_06
Patent number
US05763461

Reaction notes

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