Potassium Iodide → HCID 11785504, compound

HRID 854681Notes

Reaction equation

HRID 854681 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)[S:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[N: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]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)[O:30][CH:31]=1.[I-].[K+]>CC(=O)CC>[F:43][C:40]([F:41])([F:42])[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[S:10][CH:11]=[C:7]([CH2:6][N:1]5[CH:5]=[CH:4][N:3]=[N:2]5)[N:8]=4)=[CH:13][CH:14]=3)[N:28]=2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 690682904-Chloromethyl-2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazoleHCID 1363552324-(4-[1,2,3]Triazol-1-ylmethyl-thiazol-2-yl)-phenol

Product 1

HCID 11785504HCID 11785504, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.129 g (0.50 mmol) 4-(4-[1,2,3]triazol-1-ylmethyl-thiazol-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 0.144 g (0.50 mmol) 4-chloromethyl-2-[2-(4-trifluoromethyl-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 248 mg raw material which was purified on silica. Elution with ethyl acetate yielded 122 mg white crystals that gave, after recrystallisation from 6 ml ethanol, 79 mg (31%) pure 1-[2-(4-{2-[2-((E)-4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-thiazol-4-ylmethyl]-1H-[1,2,3]triazole melting at 163-165° 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 248 mg raw material which
  10. customwas purified on silica
  11. washElution with ethyl acetate

Sources & evidence

ORD record
ord-fe57f858f1cb4c98a9cce93b710a63d2
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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