Iodine → 3-Iodo-1H-indazole-4-carbonitrile

HRID 475139Notes

Reaction equation

HRID 475139 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]#[N:11])[C:4]=2[CH:3]=[N:2]1.[OH-].[K+].[I:14]I>CN(C=O)C>[I:14][C:3]1[C:4]2[C:5]([C:10]#[N:11])=[CH:6][CH:7]=[CH:8][C:9]=2[NH:1][N:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 247293471H-Indazole-4-carbonitrile

Product 1

HCID 1785096383-Iodo-1H-indazole-4-carbonitrileYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1H-indazole-4-carbonitrile (1.65 g, 11.1 mmol) in DMF (30 mL) was added KOH (1.86 g 33.3 mmol) and I2 (5.6 g 22.2 mmol). The mixture was stirred at RT for 5 h. The reaction mixture was quenched with water (100 mL) and extracted with EtOAc (200 mL). The extract was concentrated in vacuo to afford 3-iodo-1H-indazole-4-carbonitrile as white solid (2.01 g, 64.7%). MS (ESI): m/z=270 [M+1]+.

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with EtOAc (200 mL)
  3. concentrationThe extract was concentrated in vacuo

Sources & evidence

ORD record
ord-6841b4aac8004a41b4d0cf3d33874fd7
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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