Iodine → HCID 178526495, compound

HRID 1823915Notes

Reaction equation

HRID 1823915 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].[OH-].[K+].[I:15]I.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[I:15][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 656671Sodium Pyrosulfite

Product 1

HCID 178526495HCID 178526495, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitro-1H-indazole (10.0 g, 62.3 mmol) in DMF (120 ml) was added potassium hydroxide (12.9 g, 230.4 mmol) followed by iodine (31.1 g, 122.6 mmol) portion wise over 5 minutes. The resulting mixture was stirred at room temperature for 14 hours and then poured onto 10% sodium metabisulfite (100 ml) and extracted into ethyl acetate (3×50 ml). The combined organic extracts were washed with brine (50 ml), dried (Na2SO4) and concentrated in vacuo to afford the title compounds as a pale orange solid (17.5 g). 1H NMR (400 MHz, DMSO-d6) δ 7.77 (1H, d), 8.26 (1H, d), 8.34 (1H, s), 14.15 (1H, s). MS (ES+) m/e=290.

Workup

  1. extractionextracted into ethyl acetate (3×50 ml)
  2. washThe combined organic extracts were washed with brine (50 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f99c06c08d824ccca6cd8934e9048600
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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