Water → 5-(3,5-Dichloro-phenylsulfanyl)-1-isopropyl-4-pyridin-4-ylmethyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1862473Notes

Reaction equation

HRID 1862473 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH2:11]([O:13][C:14]([C:16]1[C:20](CBr)=[C:19]([S:23][C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=2)[N:18]([CH:32]([CH3:34])[CH3:33])[N:17]=1)=[O:15])[CH3:12].O>CN(C=O)C>[CH2:11]([O:13][C:14]([C:16]1[C:20]([CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[C:19]([S:23][C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=2)[N:18]([CH:32]([CH3:33])[CH3:34])[N:17]=1)=[O:15])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 693555624-bromomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 693539885-(3,5-Dichloro-phenylsulfanyl)-1-isopropyl-4-pyridin-4-ylmethyl-1H-pyrazole-3-carboxylic acid ethyl esterYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 55 mg of 4-(hydroxymethyl)pyridine in DMF at 0° C. was added 20 mg sodium hydride (60% in oil). To the mixture was added dropwise a solution of 229 mg of 4-bromomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester in 2 ml of N,N-dimethylformamide. After 15 min water was added and the mixture was extracted with dichloromethane (×3). The combined extracts were dried over magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography using ethyl acetate/iso-hexane for the elution to give 80 mg of 5-(3,5-dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methyl]-1H-pyrazole-3carboxylic acid ethyl ester as a colourless gum. Mass spectrum (ESI) m/z 480 [M]+.

Workup

  1. extractionthe mixture was extracted with dichloromethane (×3)
  2. dry with materialThe combined extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. washfor the elution

Sources & evidence

ORD record
ord-6fed200d381c42c78e0fb8b33f703062
Source dataset
uspto-grants-2003_03
Patent number
US06538015B1

Reaction notes

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