Sodium hydride → methyl 2-(4-bromo-1H-pyrazol-1-yl)propanoate

HRID 2266712Notes

Reaction equation

HRID 2266712 reaction equation
[H-].[Na+].[Br:3][CH:4]1[CH:8]=[N:7][N:6]=[CH:5]1.[CH3:9][O:10][C:11](=[O:15])[CH:12](Cl)[CH3:13]>CN(C=O)C>[CH3:9][O:10][C:11](=[O:15])[CH:12]([N:6]1[CH:5]=[C:4]([Br:3])[CH:8]=[N:7]1)[CH3:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28659Methyl 2-chloropropionateHCID 57919651HCID 57919651, compound

Product 1

HCID 17024860methyl 2-(4-bromo-1H-pyrazol-1-yl)propanoateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.12 g, 4.9 mmol) was added to a solution of 4-bromo-4H-pyrazole (0.60 g, 4.1 mmol) in DMF (10 mL). After stirring for 10 minutes, a solution of 2-chloro-propionic acid methyl ester in DMF (4 mL) was added. After stirring for 4 hours, the reaction was partitioned between ethyl acetate and water. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4 and concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of ethyl acetate and hexanes to afford 2-(4-bromo-pyrazol-1-yl)-propionic acid methyl ester (733 mg, 77%).

Workup

  1. stirringAfter stirring for 4 hours
  2. customthe reaction was partitioned between ethyl acetate and water
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was purified by silica gel chromatography
  8. washelution of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-918514ca1c454bcd8dffa70e64e6382c
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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