N-bromobutanimide → HCID 178497388, compound

HRID 503183Notes

Reaction equation

HRID 503183 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([F:14])=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[CH:8]2)=[O:4].[Br:15]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:6]([F:14])=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[Br:15])=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59797108methyl 4-fluoro-1H-indazole-5-carboxylate

Product 1

HCID 178497388HCID 178497388, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.2 g of 4-fluoro-1H-5-indazolecarboxylic acid methyl ester obtained in Production Example II-13-c in 20 ml dimethylformamide was added 2.12 g of N-bromosuccinimide at room temperature, and the mixture was stirred at the same temperature for 1 hour. After removing the solvent by distillation, 120 ml of ethyl acetate was added to the residue. The mixture was sequentially washed with half-saturated aqueous sodium hydrogencarbonate solution, water and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 3.0 g of the title compound as bright yellow crystals.

Workup

  1. customAfter removing the solvent
  2. distillationby distillation, 120 ml of ethyl acetate
  3. additionwas added to the residue
  4. washThe mixture was sequentially washed with half-saturated aqueous sodium hydrogencarbonate solution, water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2908cb1328124f0cb2c8eb9705db838d
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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