Iodine → HCID 178509895, compound
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction mixture was quenched with EtOAc (200 mL) and water (100 mL)
- 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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