Iodine → HCID 178505824, compound

HRID 246096Notes

Reaction equation

HRID 246096 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([F:11])[CH:3]=1.[I:12]I.[OH-].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.C(OCC)C.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:12])=[N:7][NH:8]2)=[C:4]([F:11])[CH:3]=1

Participants

8

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 247284446-Chloro-4-fluoro-1H-indazole

Product 1

HCID 178505824HCID 178505824, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

6-Chloro-4-fluoro-1H-indazole (7.6 g, 44.6 mmol) was dissolved in DMF (110 ml). Iodine (22.6 g, 89.1 mmol) was added followed by potassium hydroxide (9.5 g, 169 mmol). The reaction was stirred at room temperature for 1.5 h. Water, 1 M sodium thiosulfate solution and diethyl ether were added. The layers were separated and the aqueous layer was extracted once more with ether. The organic layers were washed with water and sodium chloride solution, and then dried over sodium sulfate. Evaporation of the solvent gave 11.16 g (85%) of 6-chloro-4-fluoro-3-iodo-1H-indazole as a light brown solid (M−H)−=295.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted once more with ether
  3. washThe organic layers were washed with water and sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a2a8828b2d854260a74ffecd18914479
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…