Iodine → 4,6-Difluoro-3-iodo-1H-indazole

HRID 246065Notes

Reaction equation

HRID 246065 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[OH-].[K+].[I:14]I>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([I:14])=[N:5][NH:6]2

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 247284234,6-Difluoro-1H-indazole

Product 1

HCID 1785059114,6-Difluoro-3-iodo-1H-indazoleYield 103.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,6-difluoro-1H-indazole (1.16 g, 7.53 mmol) in DMF (60 ml) at room temperature was added potassium hydroxide (1.27 g, 22.6 mmol) and iodine (2.87 g, 11.3 mmol). The maroon reaction mixture was stirred at room temperature for 2 h then quenched with 10% aqueous Na2S2O3 and diluted with water. The mixture was extracted with EtOAc (2×). The combined organics were washed with water, sat LiCl, and sat NaCl, then dried over MgSO4 and concentrated to afford 2.18 g of 4,6-difluoro-3-iodo-1H-indazole as a light brown solid.

Workup

  1. customThe maroon reaction mixture
  2. customthen quenched with 10% aqueous Na2S2O3
  3. additiondiluted with water
  4. extractionThe mixture was extracted with EtOAc (2×)
  5. washThe combined organics were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2576471ddc7942848132d37f0102d80d
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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