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

HRID 475120Notes

Reaction equation

HRID 475120 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

A mixture of 1H-indazole-4-carbonitrile (1.65 g, 11.1 mmol), KOH (1.86 g, 33.3 mmol), and I2 (5.6 g, 22.2 mmol) in DMF (30 mL) was stirred at RT overnight. The reaction mixture was filtered. The filtrate was diluted with water (100 mL) and extracted with EtOAc (200 mL). The organic layer 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. filtrationThe reaction mixture was filtered
  2. additionThe filtrate was diluted with water (100 mL)
  3. extractionextracted with EtOAc (200 mL)
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-46bc4deee3ea4fd38faa5626cb9e162c
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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