Iodine → HCID 178477832, compound

HRID 245961

Reaction equation

HRID 245961 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][N:6]=[CH:5]2.[OH-].[K+].[I:14]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][N:6]=[C:5]2[I:14]

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 4123035,6-dichloro-1H-indazole

Product 1

HCID 178477832HCID 178477832, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5,6-dichloro-1H-indazole (0.50 g, 2.67 mmol) in DMF (8 ml) at room temperature was added powdered potassium hydroxide (450 mg, 8.02 mmol) and iodine (1.02 g, 4.01 mmol). The maroon reaction mixture was stirred at room temperature for 45 min then quenched with 10% aqueous Na2S2O3 and diluted with water. The mixture was extracted with EtOAc (2×). The combined organics were washed with water (3×), dried over MgSO4 and concentrated to afford 827 mg (99%) of 5,6-dichloro-3-iodo-1H-indazole as a pale yellow solid. 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 13.79 (s, 1H), 7.94 (s, 1H), 7.72 (s, 1H).

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 (3×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-091bfeade6204eedbc853379d096cb9f
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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