HCID 11437094, compound → HCID 11149948, compound

HRID 1007066Notes

Reaction equation

HRID 1007066 reaction equation
[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[N:9]=2)=[CH:5][C:4]([C:16]([F:19])([F:18])[F:17])=[N:3]1.[H][H]>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH2:15])[N:9]=2)=[CH:5][C:4]([C:16]([F:19])([F:17])[F:18])=[N:3]1

Participants

5

Reactant 2

HCID 11437094HCID 11437094, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11149948HCID 11149948, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

7.00 g (26.1 mmol) of 2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-6-cyanopyridine were dissolved in 150 ml of glacial acetic acid, admixed with 1.40 g of Pd(OH)2, 20% on charcoal, and hydrogenated under a hydrogen overpressure of 17 bar. After 2 h, the catalyst was removed by filtration and the filtrate was concentrated by evaporation. The residue was taken up in water, admixed with 20 ml of 2 N HCl and subjected to multiple extraction with ethyl acetate. The aqueous phase was subsequently adjusted to a pH of 10 using 2 N NaOH and then subjected to multiple extraction with ethyl acetate. The combined organic extracts were then dried using MgSO4, filtered and concentrated.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated by evaporation
  3. extractionsubjected to multiple extraction with ethyl acetate
  4. extractionsubjected to multiple extraction with ethyl acetate
  5. customThe combined organic extracts were then dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9256358489804a9598abe91c5cd629d0
Source dataset
uspto-grants-2004_09
Patent number
US06794336B2

Reaction notes

Loading…