Potassium Carbonate → 3-[4-(3-Fluoro-benzyloxy)-phenyl]-5-imidazol-1-ylmethyl-isoxazole

HRID 72332

Reaction equation

HRID 72332 reaction equation
[N:1]1([CH2:6][C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br>CN(C=O)C>[F:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:8]=[C:7]([CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[O:11][N:10]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 1363599094-(5-Imidazol-1-ylmethyl-isoxazol-3-yl)-phenol

Product 1

HCID 468936483-[4-(3-Fluoro-benzyloxy)-phenyl]-5-imidazol-1-ylmethyl-isoxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5-imidazol-1-ylmethyl-isoxazol-3-yl)-phenol (150 mg, 0.62 mmol) and potassium carbonate (172 mg, 1.25 mmol) were placed in 10 ml of DMF, to which solution was added dropwise 3-fluorobenzyl bromide (89 μl, 0.75 mmol), and the mixture was stirred at room temperature for 4 hours. The completion of the reaction was confirmed by LC, and then DMF was distilled off under reduced pressure. A crude solid compound was extracted with ethyl acetate and water, and the organic solvent 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-(3-fluoro-benzyloxy)-phenyl]-5-imidazol-1-ylmethyl-isoxazole as a desired white solid compound.

Workup

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

Sources & evidence

ORD record
ord-0dc4c04e86034af8b952ea32690a879e
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Linked notes

Loading…