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

HRID 876822Notes

Reaction equation

HRID 876822 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-7099f185e24e4dff8ccf415a8474ccc1
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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