1,4-Dioxane → methyl 1-(3-chloropyridin-2-yl)-3-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}-1H-pyrazole-5-carboxylate

HRID 1630667Notes

Reaction equation

HRID 1630667 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH2:17][C:18]3[CH:19]=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=3)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[O:28]1CCOCC1>[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([C:17]([C:18]3[CH:19]=[N:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=3)=[O:28])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 66587532methyl 1-(3-chloropyridin-2-yl)-3-{[6-(trifluoromethyl)pyridin-3-yl]methyl}-1H-pyrazole-5-carboxylate

Product 1

HCID 66587481methyl 1-(3-chloropyridin-2-yl)-3-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

1.29 g (3.20 mmol) of methyl 1-(3-chloropyridin-2-yl)-3-{[6-(trifluoromethyl)pyridin-3-yl]methyl}-1H-pyrazole-5-carboxylate were dissolved in 80 ml of dioxane, 16.72 g (192 mmol) of manganese(IV) oxide were added and the mixture was stirred at reflux for 12 h. The mixture was filtered off with suction and the filtrate was freed from the solvent. The desired product was obtained by chromatographic purification.

Workup

  1. temperatureat reflux for 12 h
  2. filtrationThe mixture was filtered off with suction

Sources & evidence

ORD record
ord-7235d5634ab7496d8d3b47ddea095015
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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