Iodine → HCID 178468692, compound

HRID 34045Notes

Reaction equation

HRID 34045 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:15][CH3:16])=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[CH:9]2)=[O:5])[CH3:2].[I:17]I.[OH-].[K+].S([O-])(O)=O.[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:15][CH3:16])=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[I:17])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 807Iodine2×HCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 59797354CID 59797354

Product 1

HCID 178468692HCID 178468692, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 15 mL of a solution of 1.33 g of 4-methoxy-1H-indazole-5-carboxylic acid ethyl ester in N,N-dimethylformamide were added 1.95 g of iodine and 0.85 g of potassium hydroxide, stirred at room temperature for 1 hour and 40 minutes, added with another 0.8 g of iodine, and stirred for 3 hours and 20 minutes. Thereafter, 10% sodium hydrogen sulfite aqueous solution was added, extracted twice with ethyl acetate, and the organic layer was washed once with saturated brine, dried over magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography, to afford 1.68 g of the title compound as colorless crystals.

Workup

  1. stirringstirred for 3 hours and 20 minutes
  2. extractionextracted twice with ethyl acetate
  3. washthe organic layer was washed once with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe crude product was purified
  7. customseparated by silica gel column chromatography

Sources & evidence

ORD record
ord-76b38609be7a41c29b6c85e3479acf20
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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