Potassium Iodide → 4-[1,2,3]triazol-1-yl-1-(4-{2-[(E)-2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butan-1-one

HRID 1182185Notes

Reaction equation

HRID 1182185 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[N:13]2)=[CH:4][CH:3]=1.CC(=O)CC.Cl[CH2:24][C:25]1[N:26]=[C:27](/[CH:30]=[CH:31]/[C:32]2[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][CH:33]=2)[O:28][CH:29]=1.[I-].[K+]>>[N:12]1([CH2:11][CH2:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:24][C:25]3[N:26]=[C:27](/[CH:30]=[CH:31]/[C:32]4[CH:33]=[CH:34][C:35]([O:38][C:39]([F:42])([F:40])[F:41])=[CH:36][CH:37]=4)[O:28][CH:29]=3)=[CH:3][CH:4]=2)=[O:17])[CH:16]=[CH:15][N:14]=[N:13]1

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 6569Methyl Ethyl KetoneHCID 222420804-chloromethyl-2-[(E)-2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazoleHCID 587108001-(4-Hydroxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one

Product 1

HCID 115550774-[1,2,3]triazol-1-yl-1-(4-{2-[(E)-2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butan-1-one

Conditions

Temperature
60 °C

Procedure

To a solution of 116 mg (0.5 mmol) 1-(4-hydroxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one in 10 ml 2-butanone 98 mg (0.3 mmol) cesium carbonate was added and the mixture was stirred at 60° C. for 30 minutes. Then 152 mg (0.5 mmol) 4-chloromethyl-2-[(E)-2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazole and 83 mg (0.5 mmol) potassium iodide were added and the mixture was stirred at 60° C. overnight. After removal of all volatiles in vacuo the residue was purified by column chromatography on silica (ethyl acetate) to give 4-[1,2,3]triazol-1-yl-1-(4-{2-[(E)-2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butan-1-one. Yield: 200 mg (81%) white solid.

Workup

  1. stirringthe mixture was stirred at 60° C. overnight
  2. customAfter removal of all volatiles in vacuo the residue
  3. customwas purified by column chromatography on silica (ethyl acetate)

Sources & evidence

ORD record
ord-0f2b5e315a8c48ffb085b0eaee2cab09
Source dataset
uspto-grants-2007_10
Patent number
US07288557B2

Reaction notes

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