5-Nitroindazole → HCID 178526495, compound

HRID 1430934Notes

Reaction equation

HRID 1430934 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 rt for 72 h. The reaction mixture was diluted with EtOAc and washed with sat'd 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 sat'd sodium bisulfite solution, water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-03b9dc4f46a94cc694ac9a9d26e60adb
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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