Water → HCID 20121074, compound

HRID 889164Notes

Reaction equation

HRID 889164 reaction equation
[N:1]1[NH:2][C:3](=[O:10])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH2:11]([CH:13]1[O:15][CH2:14]1)Br.[H-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[O:15]1[CH2:14][CH:13]1[CH2:11][N:2]1[C:3](=[O:10])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1]1

Participants

7

Reactant 4

HCID 962WaterHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 814311,2,4-Triazolo(4,3-a)pyridin-3(2H)-one

Product 1

HCID 20121074HCID 20121074, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 2H-[1,2,4]triazolo[4,3-a]pyridin-3-one (CAS 6969-71-7) (1.0 g) and epibromohydrin (1.27 ml) in N,N-dimethylformamide (10 ml), sodium hydride (60% in oil) (326 mg) was added and the mixture was stirred at room temperature for 14 hours. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography. The obtained solid was washed with n-heptane to obtain the title compound (290 mg).

Workup

  1. additionwas added
  2. washThe organic layer was washed with water and brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washThe obtained solid was washed with n-heptane

Sources & evidence

ORD record
ord-57737475265f44e7b9fd620c3bb4479e
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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