Iodine → HCID 178526495, compound

HRID 1711424Notes

Reaction equation

HRID 1711424 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].[I:13]I.[OH-].[K+].OS([O-])=O.[Na+]>CN(C=O)C>[I:13][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

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 215015-NitroindazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 178526495HCID 178526495, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-nitroindazole (8.50 g, 52.13 mmol) in DMF was treated with iodine (26.46 g, 104.27 mmol) and potassium hydroxide pellets (11.70 g, 208.54 mmol) at room temperature, stirred for 4 days, poured into NaHSO3 solution (11.06 g in 200 mL water) and filtered. The filtercake was washed with water and dried in vacuo to provide the title compound as a yellow solid, 14.74 g (98% yield), characterized by NMR and mass spectral analyses.

Workup

  1. filtrationfiltered
  2. washThe filtercake was washed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-76626455e9c349eabeb317ab6da9f2d4
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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