N-bromobutanimide → HCID 57990193, compound

HRID 245609Notes

Reaction equation

HRID 245609 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:14])=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4].[Br:15]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:14])=[C:7]([Br:15])[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12637848Methyl 6-amino-1H-indazole-7-carboxylate

Product 1

HCID 57990193HCID 57990193, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3.4 g (17.78 mmol) of 6-amino-1H-indazole-7-carboxylic acid methyl ester, prepared as in step a in example 10, in 34 mL of N,N-dimethylformamide is added 3.16 g (17.78 mmol) of N-bromosuccinimide. The reaction is stirred at ambient temperature 4 hours. After concentration in vacuo the residue is triturated in ethyl acetate and after filtration 3.38 g of a brownish solid are obtained. The filtrate is evaporated and submitted to column chromatography purification on silica gel with hexanes and ethyl acetate as eluents to afford 563 mg of a white solid. In totality 3.95 g (82%) of a product are obtained; LC/MS:270/272 (M+H)+.

Workup

  1. concentrationAfter concentration in vacuo the residue
  2. customis triturated in ethyl acetate
  3. filtrationafter filtration 3.38 g of a brownish solid
  4. customare obtained
  5. customThe filtrate is evaporated
  6. customsubmitted to column chromatography purification on silica gel with hexanes and ethyl acetate as eluents

Sources & evidence

ORD record
ord-f5aa1c5169dc4ce9b9a0ac44150d4bc0
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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