Potassium Iodide → 1-[4-(4-{2-[2-(E)-(2-Fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole

HRID 1296549Notes

Reaction equation

HRID 1296549 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[F:20])[O:6][CH:7]=1.[N:21]1([CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)[CH:25]=[CH:24][N:23]=[N:22]1.[I-].[K+].C[O-].[Na+]>CO>[F:20][C:11]1[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:10]=1/[CH:9]=[CH:8]/[C:5]1[O:6][CH:7]=[C:3]([CH2:2][O:36][C:33]2[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][CH2:27][CH2:26][N:21]3[CH:25]=[CH:24][N:23]=[N:22]3)=[CH:31][CH:32]=2)[N:4]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 690723654-Chloromethyl-2-[2-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazole

Product 1

HCID 114545761-[4-(4-{2-[2-(E)-(2-Fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.305 g (1.00 mmol) 4-Chloromethyl-2-[2-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazole, 0.217 g 1.00 mmol) 4-(4-[1,2,3]triazol-1-yl-butyl)-phenol, 0.166 g (1.00 mmol) potassium iodide and 0.191 ml (1.00 mmol) of a 30% sodium methylate solution were added to 50.0 ml methanol and heated to reflux for 10 h. After removal of solvent, partitioning of the residue between 50 ml ethyl acetate and 15 ml water, the organic phase was washed 3× with 15 ml 1 N NaOH, twice with 15 ml water and dried over sodium sulphate. The solution was evaporated to dryness and the residue purified by reversed phase HPLC (C4-column, eluent: methanol/water 8:2+0.2% acetic acid). After evaporation and drying of the product containing fractions, the residue was treated with diethyl ether and dried in vacuo at 40° C. 80 mg (16%) 1-[4-(4-{2-[2-(2-Fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole.

Workup

  1. temperatureheated
  2. temperatureto reflux for 10 h
  3. customAfter removal of solvent
  4. custompartitioning of the residue between 50 ml ethyl acetate and 15 ml water
  5. washthe organic phase was washed 3× with 15 ml 1 N NaOH
  6. dry with materialtwice with 15 ml water and dried over sodium sulphate
  7. customThe solution was evaporated to dryness
  8. customthe residue purified by reversed phase HPLC (C4-column, eluent: methanol/water 8:2+0.2% acetic acid)
  9. customAfter evaporation
  10. customdrying of the product
  11. additioncontaining fractions
  12. additionthe residue was treated with diethyl ether
  13. customdried in vacuo at 40° C

Sources & evidence

ORD record
ord-b529a9344b284164a58b33836243fd9e
Source dataset
uspto-grants-2007_07
Patent number
US07247649B2

Reaction notes

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