HCID 18406865, compound → HCID 72207223, compound

HRID 1615625Notes

Reaction equation

HRID 1615625 reaction equation
[N:1]1[C:2]([CH2:10][OH:11])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12>CCO.[O-2].[Mn+4].[O-2]>[N:1]1[C:2]([CH:10]=[O:11])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 1

HCID 18406865HCID 18406865, compound

Product 1

HCID 72207223HCID 72207223, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of [1,2,4]triazolo[1,5-a]pyridin-2-ylmethanol (0.35 g, 2.3 mmol) in EtOH (50 mL) was added manganese (IV) oxide (1.02 g, 11.5 mmol). The mixture was refluxed for 2 days. After cooling to room temperature, the mixture was filtered through Celite. The filtrate was concentrated, and the residue was purified by reverse phase column chromatography (eluting with 10% v/v acetonitrile in water, with 0.01% NH3.H2O) to afford the title compound (0.15 g, 43% yield) as a white solid. ESI MS: m/z 148 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed for 2 days
  2. filtrationthe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by reverse phase column chromatography (
  5. washeluting with 10% v/v acetonitrile in water, with 0.01% NH3.H2O)

Sources & evidence

ORD record
ord-770550ffb68f4471a8d3f521eff936c9
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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