Iodine → HCID 178488727, compound

HRID 1351993Notes

Reaction equation

HRID 1351993 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[CH:8]2.[I:12]I.[OH-].[K+].S([O-])(O)=O.[Na+]>CN(C)C=O>[I:12][C:8]1[C:7]2[C:11](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[NH:10][N:9]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 104418397-MethoxyindazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 178488727HCID 178488727, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-methoxy-1H-indazole (2.60 g, 17.5 mmol) in N,N-dimethylformamide (50 mL) are added iodine (6.68 g, 26.3 mmol) and potassium hydroxide (2.79 g, 49.7 mmol), and the mixture is stirred at room temperature for 0.5 hour. The reaction solution is poured into a 10% aqueous sodium hydrogen sulfite solution (200 mL), and the mixture is extracted with diethyl ether. The organic layer is washed with water and a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is evaporated under reduced pressure, and the obtained residue is purified by silica gel column chromato-graphy (n-hexane/ethyl acetate=5/1) to give the title compound (3.97 g, yield: 83%).

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. washThe organic layer is washed with water
  3. dry with materiala saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent is evaporated under reduced pressure
  5. customthe obtained residue is purified by silica gel column chromato-graphy (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-6c09596217b042a3889f37c1ddc5ed3e
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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