Iodine → HCID 178509895, compound

HRID 475150Notes

Reaction equation

HRID 475150 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5]2[CH:6]=[N:7][NH:8][C:9]=2[CH:10]=1.[OH-].[K+].[I:15]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5]2[C:6]([I:15])=[N:7][NH:8][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 86694708HCID 86694708, compound

Product 1

HCID 178509895HCID 178509895, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-chloro-1H-indazole-4-carbonitrile (2.0 g, 11.26 mmol) in DMF (30 mL) was added KOH (1.89 g, 33.78 mmol) and I2 (5.72 g, 22.52 mmol). The mixture was heated at 50° C. overnight. The reaction mixture was quenched with EtOAc (200 mL) and water (100 mL). The organic layer was concentrated in vacuo to afford 6-chloro-3-iodo-1H-indazole-4-carbonitrile as white solid (2.01 g, 58.8%). MS (ESI): m/z=304 [M+1]+.

Workup

  1. customThe reaction mixture was quenched with EtOAc (200 mL) and water (100 mL)
  2. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-8433ffb444a643b28a68dbd5f2f2310b
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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