Chlorosuccinimide → 6-amino-5-chloro-1H-indazole-7-carboxylic acid methyl ester

HRID 245608Notes

Reaction equation

HRID 245608 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].[Cl:15]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:14])=[C:7]([Cl:15])[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 12637848Methyl 6-amino-1H-indazole-7-carboxylate

Product 1

HCID 579901436-amino-5-chloro-1H-indazole-7-carboxylic acid methyl esterYield 36.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 1.66 g (8.71 mmol) of 6-amino-1H-indazole-7-carboxylic acid methyl ester in 17 mL of N,N-dimethylformamide, is added 1.21 g (8.71 mmol) of N-chlorosuccinimide. The mixture is stirred during 4 hours at 50° C. and then the solvent is evaporated. The residue is precipitated in ethyl acetate and after filtration and washings with ethyl acetate, 927 mg of a pure white solid are obtained. The filtrate is evaporated and submitted to a flash chromatography which gives an additional 723 mg of the compound. In totality, 1.65 g (84%) of a product are obtained as a white solid; LC/MS:226/228 (M+H)+.

Workup

  1. customthe solvent is evaporated
  2. customThe residue is precipitated in ethyl acetate
  3. filtrationafter filtration and washings with ethyl acetate, 927 mg of a pure white solid
  4. customare obtained
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-14727564fbaf4eeba5dfe92c587a2756
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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