Potassium Iodide → HCID 69424149, compound

HRID 1296546Notes

Reaction equation

HRID 1296546 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:24][C:25]1[N:26]=[C:27]([CH:30]=[CH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([F:39])[CH:33]=2)[O:28][CH:29]=1.[I-].[K+]>CC(=O)CC>[Cl:38][C:35]1[CH:36]=[CH:37][C:32](/[CH:31]=[CH:30]/[C:27]2[O:28][CH:29]=[C:25]([CH2:24][O:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[N:2]4)=[CH:15][CH:14]=3)[N:26]=2)=[CH:33][C:34]=1[F:39]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 69423427HCID 69423427, compound

Product 1

HCID 69424149HCID 69424149, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.16 g (0.74 mmol) 4-(4-[1,2,3]triazol-1-yl-butyl)-phenol and 0.14 g cesium carbonate in 20 ml 2-butanone was stirred at 60° C. for 30 min, then 0.20 g (0.74 mmol) 4-chloromethyl-2-[2-(4-chloro-3-fluoro-phenyl)-vinyl]-oxazole and 0.123 g (0.74 mmol) potassium iodide were added and stirring at 60° C. continued over night. After evaporation, 15 ml water was added and the mixture extracted thrice with 15 ml ethyl acetate. The combined organic layers were washed with 1N sodium hydroxide and water, dried over sodium sulfate and evaporated to give 350 mg raw material which was purified on silica gel. Elution with heptane/ethyl acetate 1:1 yielded 167 mg (50%) 1-[4-(4-{2-[2-(E)-(4-chloro-3-fluoro-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole as white solid melting at 146-149° C.

Workup

  1. stirringstirring at 60° C.
  2. waitcontinued over night
  3. customAfter evaporation, 15 ml water
  4. additionwas added
  5. extractionthe mixture extracted thrice with 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 350 mg raw material which
  10. customwas purified on silica gel
  11. washElution with heptane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-3f75a02de08a4fe5b21e32596047f5d7
Source dataset
uspto-grants-2007_07
Patent number
US07247649B2

Reaction notes

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