Water → HCID 86594267, compound

HRID 2377993Notes

Reaction equation

HRID 2377993 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9](C2C=CC(F)=CC=2)=[N:8][NH:7][N:6]=1)=[O:4].[H-].[Na+].O.[CH2:20]1COCC1>>[CH3:1][O:2][C:3]([C:5]1[NH:6][NH:7][N:8]([CH3:20])[CH:9]=1)=[O:4]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 66968205HCID 66968205, compound

Product 1

HCID 86594267HCID 86594267, compoundYield 33%

Procedure

5-(4-Fluoro-phenyl)-2H-[1,2,3]triazole-4-carboxylic acid methyl ester (2.21 g, 10 mmol) in THF (10 ml) was added drop-wise to an ice-cooled slurry of sodium hydride (0.42 g, 60% dispersion in mineral oil, 10 mmol) in TEF (45 ml), under argon. After stirring at room temperature for 1 h, the reaction mixture was heated at 80° C. for 16 h. Water was added to the cooled mixture and the product was extracted with diethyl ether (2×). The combined organics were washed with brine, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (silica gel, 10-50% ethyl acetate-pentane) afforded 5-4-Fluoro-phenyl)-1-methyl-2H-[1,2,3]triazole4-carboxylic acid methyl ester (763 mg, 33%) and the title compound (943 mg, 40%).

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for 16 h
  2. extractionthe product was extracted with diethyl ether (2×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4cf4d4bf960e4d22abcef12cfe7df2f3
Source dataset
uspto-grants-2008_12
Patent number
US07470710B2

Reaction notes

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