Imidazole → 3-(4-Benzyloxy-phenyl)-5-imidazol-1-ylmethyl-isoxazole

HRID 72331Notes

Reaction equation

HRID 72331 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20]OS(C)(=O)=O)[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1.C(=O)([O-])[O-].[K+].[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][N:26]3[CH:30]=[CH:29][N:28]=[CH:27]3)[O:17][N:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 59667381Methanesulfonic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester

Product 1

HCID 468937783-(4-Benzyloxy-phenyl)-5-imidazol-1-ylmethyl-isoxazole

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

Methanesulfonic acid-3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester (600 mg, 1.67 mmol), imidazole (170 mg, 2.50 mmol), potassium carbonate (460 mg, 3.34 mmol), and TBAI (200 mg, 0.54 mmol) were placed in 20 ml of DMF and stirred for 2 hours. The completion of the reaction was confirmed by LC, and then a crude solid compound obtained from distillation of the DMF under reduced pressure was extracted with ethyl acetate and water. The ethyl acetate was distilled off under reduced pressure to obtain a white solid compound. The compound was purified by silica chromatography (methylene chloride:MeOH=20:1) to obtain 3-(4-benzyloxy-phenyl)-5-imidazol-1-ylmethyl-isoxazole as a white solid compound.

Workup

  1. extractionwas extracted with ethyl acetate and water
  2. distillationThe ethyl acetate was distilled off under reduced pressure
  3. customto obtain a white solid compound
  4. customThe compound was purified by silica chromatography (methylene chloride:MeOH=20:1)

Sources & evidence

ORD record
ord-76dcf39e19b440bcbcb98d072d97b2d3
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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