Potassium Iodide → 1-[2-(4-{2-[(E)-2-(4-Pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-oxazole-4-ylmethyl]-1H-[1,2,3]triazole

HRID 854699Notes

Reaction equation

HRID 854699 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]=[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]([S:40]([F:45])([F:44])([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)[O:30][CH:31]=1.[I-].[K+]>CC(=O)CC>[F:43][S:40]([F:41])([F:42])([F:44])([F:45])[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]=[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 865985174-Chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazoleHCID 1363552314-(4-[1,2,3]Triazol-1-ylmethyl-oxazol-2-yl)-phenol

Product 1

HCID 114897411-[2-(4-{2-[(E)-2-(4-Pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-oxazole-4-ylmethyl]-1H-[1,2,3]triazoleYield 40.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 97 mg (0.40 mmol) 4-(4-[1,2,3]triazol-1-ylmethyl-oxazol-2-yl)-phenol and 78 mg (0.24 mmol) cesium carbonate in 10 ml butanone was stirred at 60° C. for 30 min, then 140 mg (0.40 mmol) 4-chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole and 66 mg (0.40 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 three 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 yield 89 mg (40%) pure title compound as light yellow solid melting at 172-174° 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 three 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-65f03bd8c04446ecb45245eaf1456842
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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