Iodine → HCID 178519380, compound

HRID 2400965Notes

Reaction equation

HRID 2400965 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[OH-].[K+].[I:14]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.O>[I:14][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=2)[NH:1][N:2]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 212506441H-Indazole-5-carboxaldehyde

Product 1

HCID 178519380HCID 178519380, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of 1H-indazol-5-carbaldehyde (34 mmol) and KOH (37 mmol) in DMF (50 mL) was added I2 (37 mmol) portionwise over 30 min. The mixture was allowed to warm to rt for 6 h. Water was added and then sat. Na2S2O3 solution was added to quench excess I2. The aqueous solution was extracted with EtOAc and the organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (EtOAc/hexane) to afford 3-iodo-1H-indazol-5-carbaldehyde.

Workup

  1. customto quench excess I2
  2. extractionThe aqueous solution was extracted with EtOAc
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-b27cec91d23841a697f66c21f04ca480
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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