Sodium Methoxide → 7-Methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine-4-carbaldehyde

HRID 2357903Notes

Reaction equation

HRID 2357903 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[C:6]2[C:7]([CH:12]=[O:13])=[CH:8][CH:9]=[C:10](I)[N:5]2[N:4]=1.[CH3:17][O-:18].[Na+]>CO>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[C:6]2[C:7]([CH:12]=[O:13])=[CH:8][CH:9]=[C:10]([O:18][CH3:17])[N:5]2[N:4]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 593892992-Trifluoromethyl-4-formyl-7-iodo-pyrazolo[1,5-a]pyridine

Product 1

HCID 593893517-Methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine-4-carbaldehydeYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of Example 113 (2.97 g) was dissolved in methanol (50.0 mL). To this solution, sodium methoxide (1.42 g) was added and the mixture was stirred for 2 hours under reflux. After cooling, the solvent was evaporated. Water was added to the resulting residue and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was suspended in diisopropyl ether. The solid product was collected by filtration to afford the title compound as a yellowish green powder (1.93 g).

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. additionWater was added to the resulting residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed sequentially with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. filtrationThe solid product was collected by filtration

Sources & evidence

ORD record
ord-e4af3c76efc441d3a04a47b4939e04ee
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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