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

HRID 53208Notes

Reaction equation

HRID 53208 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-493bf71643af4a1398f5dd4695c1f4ad
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

Loading…