Iodine → HCID 178509534, compound

HRID 246292Notes

Reaction equation

HRID 246292 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[OH-].[K+].[I:14]I>CN(C=O)C>[I:14][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]#[N:11])[CH:5]=2)[NH:1][N:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 111263841H-Indazole-5-carbonitrile

Product 1

HCID 178509534HCID 178509534, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 25 ml round-bottomed flask, 1H-indazole-5-carbonitrile (400 mg, 2.79 mmol) was dissolved in DMF (7 ml). Potassium hydroxide (607 mg, 10.8 mmol) was added followed by iodine (1.42 g, 5.59 mmol). The dark brown suspension was stirred at room temperature for 3 h then was quenched with 10% aqueous NaHSO3 and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated to give 396 mg (53%) of 3-iodo-1H-indazole-5-carbonitrile as a light yellow powder.

Workup

  1. customthen was quenched with 10% aqueous NaHSO3
  2. extractionextracted with diethyl ether (2×)
  3. washThe combined organic layers were washed twice with water and once with brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c2b291e73e01467881b4b5381f73f74f
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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