Potassium Iodide → 1-[2-(4-{2-[(E)-2-(-4-Trifluoromethylsulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-oxazol-4-ylmethyl]-1H-imidazole

HRID 854692Notes

Reaction equation

HRID 854692 reaction equation
[N:1]1([CH2:6][C:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[O:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:26][C:27]1[N:28]=[C:29]([CH:32]=[CH:33][C:34]2[CH:39]=[CH:38][C:37]([S:40]([C:42]([F:45])([F:44])[F:43])=[O:41])=[CH:36][CH:35]=2)[O:30][CH:31]=1.[I-].[K+]>CC(=O)CC>[F:45][C:42]([F:43])([F:44])[S:40]([C:37]1[CH:38]=[CH:39][C:34](/[CH:33]=[CH:32]/[C:29]2[O:30][CH:31]=[C:27]([CH2:26][O:18][C:15]3[CH:16]=[CH:17][C:12]([C:9]4[O:10][CH:11]=[C:7]([CH2:6][N:1]5[CH:5]=[CH:4][N:3]=[CH:2]5)[N:8]=4)=[CH:13][CH:14]=3)[N:28]=2)=[CH:35][CH:36]=1)=[O:41]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazoleHCID 1363431914-(4-Imidazol-1-ylmethyl-oxazol-2-yl)-phenol

Product 1

HCID 117860361-[2-(4-{2-[(E)-2-(-4-Trifluoromethylsulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-oxazol-4-ylmethyl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.121 g (0.50 mmol) 4-(4-imidazol-1-ylmethyl-oxazol-2-yl)-phenol and 0.10 g (0.30 mmol) cesium carbonate in 10 ml butanone was stirred at 60° C. for 30 min, then 0.168 g (0.50 mmol) 4-chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole and 0.083 g (0.50 mmol) potassium iodide were added and stirring at 60° C. continued over night. After evaporation, 15 ml water was added and the mixture extracted with two portions of 15 ml ethyl acetate. The combined organic layers were washed with 1N sodium hydroxide and water, dried over sodium sulfate and evaporated to give, after recrystallisation from 2-propanol, 121 mg (45%) of the title compound as light brown crystals melting at 134-136° C.

Workup

  1. stirringstirring at 60° C.
  2. waitcontinued over night
  3. customAfter evaporation, 15 ml water
  4. additionwas added
  5. extractionthe mixture extracted with two portions of 15 ml ethyl acetate
  6. washThe combined organic layers were washed with 1N sodium hydroxide and water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto give
  10. customafter recrystallisation from 2-propanol, 121 mg (45%) of the title compound as light brown crystals melting at 134-136° C.

Sources & evidence

ORD record
ord-9ff2f1e6199f4de68d34c49e03a65fa0
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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