Sodium Hydroxide → 1-(Pyrazolo[1,5-a]pyridin-5-yl)ethanone

HRID 1890573Notes

Reaction equation

HRID 1890573 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]2[N:10]=[CH:11][C:12](C(OC)=O)=[C:6]2[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+]>OS(O)(=O)=O>[N:10]1[N:7]2[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][C:6]2=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67305299Methyl 5-acetylpyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 673052451-(Pyrazolo[1,5-a]pyridin-5-yl)ethanoneYield 38.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of methyl 5-acetylpyrazolo[1,5-a]pyridine-3-carboxylate (3-2) (90 mg, 0.41 mmol) dissolved in 50% H2SO4 (2 mL) was stirred at 80° C. for 3 h. After cooled to 0° C., the solution was treated with 5N NaOH solution, and then extracted with Et2O. The organic layer was separated, dried, concentrated and purified by flash chromatography to afford the title compound (25 mg).

Workup

  1. temperatureAfter cooled to 0° C.
  2. extractionextracted with Et2O
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-31723c4c58ab46e5b807c9d8bd4bd3d5
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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