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

HRID 854691Notes

Reaction equation

HRID 854691 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:41]([F:44])([F:43])[F:42])=[CH:36][CH:35]=2)[O:30][CH:31]=1.[I-].[K+]>CC(=O)CC>[F:44][C:41]([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)([F:42])[F:43]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 691129774-Chloromethyl-2-[2-(4-trifluoromethylsulfanyl-phenyl)-vinyl]-oxazoleHCID 1363431914-(4-Imidazol-1-ylmethyl-oxazol-2-yl)-phenol

Product 1

HCID 112032511-[2-(4-{2-[(E)-2-(-4-Trifluoromethylsulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-oxazol-4-ylmethyl]-1H-imidazoleYield 42%

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 0.160 g (0.50 mmol) 4-chloromethyl-2-[2-(4-trifluoromethylsulfanyl-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 110 mg (42%) of the title compound as light brown crystals melting at 144-145° C. (from 2-propanol).

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

Sources & evidence

ORD record
ord-db29745e47964eb7b87909a6d4ab4a93
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

Loading…