HCID 86692440, compound → HCID 86692439, compound

HRID 1748472Notes

Reaction equation

HRID 1748472 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([CH:19]=[CH2:20])=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]>O1CCOCC1.[C].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([CH2:19][CH3:20])=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 86692440HCID 86692440, compound

Product 1

HCID 86692439HCID 86692439, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

10% Palladium-carbon (containing ca. 50% water; 281 mg) was added to a solution of 1-(3-chloro-5-vinylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (567 mg) in 1,4-dioxane (19 ml), and stirred under hydrogen atmosphere at room temperature for an hour. The reaction solution was filtered through Celite and the filtrate was concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-(3-chloro-5-ethylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (459 mg).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c596e107e66d4cf6bc756277a94be859
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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