5-Nitroindazole → HCID 178526495, compound

HRID 921754Notes

Reaction equation

HRID 921754 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C1C(=O)N([I:20])C(=O)C1>CN(C=O)C.CCOC(C)=O>[I:20][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][N:8]=1

Participants

5

Reactant 2

HCID 215015-NitroindazoleHCID 120273N-Iodosuccinimide

Product 1

HCID 178526495HCID 178526495, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-nitro-1H-indazole (2 g, 12.26 mmol) was taken up in DMF (40 mL) and NIS (5.52 g, 24.52 mmol) was added. The reaction was stirred at room temperature for 72 h. The reaction mixture was diluted with EtOAc and washed with saturated sodium bisulfite solution, water, and then 2× with brine. The organic layer was dried over Na2SO4, filtered and concentrated to give 3-iodo-5-nitro-1H-indazole (3.4 g) as a yellow solid.

Workup

  1. washwashed with saturated sodium bisulfite solution, water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f0c29f830ed34eeb93ad42ce034e517f
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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