Triethylamine → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

HRID 2283187Notes

Reaction equation

HRID 2283187 reaction equation
C(N(CC)CC)C.Cl[C:9]1[N:13]([CH3:14])[N:12]=[C:11]([CH:15]([F:17])[F:16])[C:10]=1[CH:18]=[O:19]>C(O)C.[Pd]>[CH3:14][N:13]1[CH:9]=[C:10]([CH:18]=[O:19])[C:11]([CH:15]([F:16])[F:17])=[N:12]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 197546925-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 533020643-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehydeYield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

In an autoclave, 10 g of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde were dissolved in 150 ml of ethanol, and 10.4 g of triethylamine and 500 mg of 5% palladium on calcium carbonate were added. The autoclave was flushed with nitrogen and subsequently pressurised to 5 bar hydrogen. The reaction mixture was then stirred at 30° C. for 4 h. After filtration of the catalyst, the solvent was removed under reduced pressure and the product was obtained as a solid (7.4 g) having a melting point of 46-47° C.

Workup

  1. customThe autoclave was flushed with nitrogen
  2. filtrationAfter filtration of the catalyst
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1fd79fa2c380483389fd7c208331b22d
Source dataset
uspto-grants-2015_09
Patent number
US09145369B2

Reaction notes

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