Iodine → HCID 178505879, compound

HRID 230143Notes

Reaction equation

HRID 230143 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[N:10]=[CH:9][C:8]2[CH:11]=[N:12][NH:13][C:7]=2[CH:6]=1.[I:19]I.[OH-].[K+]>CN(C=O)C>[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[N:10]=[CH:9][C:8]2[C:11]([I:19])=[N:12][NH:13][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 807Iodine2×HCID 14797Potassium HydroxideHCID 59834356HCID 59834356, compound

Product 1

HCID 178505879HCID 178505879, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution of 6-(2,4-difluorophenoxy)-1H-pyrazolo[4,3-c]pyridine (0.10 g) in DMF was added 0.11 g of iodine and 0.049 g of potassium hydroxide. After 5 hours, additional 10% of iodine was added and a reaction mixture was stirred for an additional one hour. The mixture was quenched with 1 M sodium bisulfite (50 mL) solution and extracted with ethyl acetate (3×30 mL). The organic layers were combined, dried over MgSO4, and concentrated to give 0.11 g of 6-(2,4-difluorophenoxy)-3-iodo-1H-pyrazolo[4,3-c]pyridine (71% yield). Mass Spec. M+H=374.

Workup

  1. customThe mixture was quenched with 1 M sodium bisulfite (50 mL) solution
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-390b47fa6e8d4681be267a4217268d43
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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