N-bromobutanimide → HCID 178498689, compound

HRID 706581Notes

Reaction equation

HRID 706581 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][C:13]=1[F:14])=[O:4].[Br:15]N1C(=O)CCC1=O>CN(C=O)C>[Br:15][C:7]1[C:6]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:13]([F:14])[CH:12]=[CH:11][C:10]=2[NH:9][N:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 593345601383474-59-6

Product 1

HCID 178498689HCID 178498689, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl-5-fluoro-1H-indazole-4-carboxylate (0.475 g, 2.45 mmol) in 25 mL of DMF was added N-bromosuccinimide (0.566 g, 3.18 mmol). This mixture was stirred at ambient temperature for one hour, then quenched with water. This mixture was extracted with EtOAc, and the combined organic extracts washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (1:1 EtOAc/Hexane) afforded 0.459 g (69%) of the title compound.

Workup

  1. customquenched with water
  2. extractionThis mixture was extracted with EtOAc
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acba70997fb7495e8c4fe10424b11020
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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