Iodine → HCID 178519380, compound

HRID 218453Notes

Reaction equation

HRID 218453 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-].[Na+].[I:14]I>O1CCOCC1.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

6

Reactant 3

HCID 807Iodine2×HCID 14798Sodium HydroxideHCID 212506441H-Indazole-5-carboxaldehyde

Product 1

HCID 178519380HCID 178519380, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1H-indazole-5-carboxaldehyde (3.75 g, 25.7 mmol) in dioxane (120 mL) was added a solution of NaOH (15.48 g, 384.9 mmol) in water (120 mL). To this solution, iodine (8.2 g, 32 mmol) was added. After 1 hr at rt, more iodine (8.2 g, 32 mmol) was added, and the reaction mixture was stirred for an additional 1 hr at rt. After removal of most of the dioxane in vacuo, the reaction mixture was extracted with EtOAc, washed with brine, dried, and concentrated. The crude product was purified by flash chromatography to afford 3-iodo-1H-indazole-5-carboxaldehyde (4.5 g, 64.5%).

Workup

  1. customAfter removal of most of the dioxane in vacuo
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-95be1ffb397d42808583323e2778abd2
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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