Ethanol → HCID 86692430, compound

HRID 1748460Notes

Reaction equation

HRID 1748460 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:13]([Cl:20])=[N:14][CH:15]=[C:16]([CH:18]=[CH2:19])[CH:17]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].C(O)C>[C].[Pd].O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:13]([Cl:20])=[N:14][CH:15]=[C:16]([CH2:18][CH3:19])[CH:17]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 86692428HCID 86692428, compound

Product 1

HCID 86692430HCID 86692430, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Next, 1-(2-chloro-5-vinylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.902 g) was added to a mixed solvent of ethanol (10 ml) and 1,4-dioxane (8 ml), the atmosphere in the flask was substituted with nitrogen gas, 10% palladium-carbon (containing ca. 50% water; 0.20 g) was added and the mixture was stirred under hydrogen atmosphere at room temperature for three hours. The reaction mixture was filtered through Celite to remove palladium-carbon, the filtrate was concentrated and the residue was purified with column chromatography (n-hexane/ethyl acetate) to give 1-(2-chloro-5-ethylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.639 g).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through Celite
  3. customto remove palladium-carbon
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified with column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bfa2cd6a0fd0402d992a79e09245ee69
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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