Water → ethyl 5-bromo-2H-indazole-3-carboxylate

HRID 34093Notes

Reaction equation

HRID 34093 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.O.[C:20](OCC)(=O)[CH3:21]>C(O)C>[CH2:20]([O:12][C:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[NH:7][N:6]=1)=[O:13])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 71573585-bromo-1H-indazole-3-carboxylic Acid

Product 1

HCID 12689364ethyl 5-bromo-2H-indazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3 g of 5-bromo-1H-indazole-3-carboxylic acid was dissolved in 60 mL of ethanol, added with 0.6 mL of concentrated sulfuric acid, and heated under reflux for 8 hours. After allowing to cool to room temperature, addition of water and extraction with ethyl acetate were conducted, and the resultant organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and the solvent was evaporated, to afford 2.7 g of the title compound as yellow crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 hours
  3. washthe resultant organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d77850c85fd540af9825519a7b12cb14
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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