Potassium Hydroxide → HCID 178497596, compound

HRID 1677696Notes

Reaction equation

HRID 1677696 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[N:8][NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4].[Br:14]N1C(=O)CCC1=O.[OH-].[K+]>CN(C=O)C.[Cl-].[NH4+]>[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:7]([Br:14])=[N:8][NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 67184N-bromobutanimideHCID 6623327methyl 1H-indazole-4-carboxylate

Product 1

HCID 178497596HCID 178497596, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 1H-indazole-4-carboxylic acid methyl ester (380 mg, 2.2 mmol) in DMF (5 mL) was added N-bromosuccinimide (NBS) (976 mg, 4.32 mmol) and KOH (485 mg, 8.64 mmol). After 1 hour, the reaction mixture was diluted with saturated aqueous ammonium chloride (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine (20 mL), dried over sodium sulfate and concentrated in vacuo to afford the title compound as a solid.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate and brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-868e1f4b18ec42bbbdb3b0a209633251
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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