Iodine → HCID 58542506, compound

HRID 1843089Notes

Reaction equation

HRID 1843089 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:10]([CH3:11])[N:9]=[C:8]([CH:12]2[CH2:14][CH2:13]2)[CH:7]=1)=[O:5])[CH3:2].[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[I:37]I>C(#N)C.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:10]([CH3:11])[N:9]=[C:8]([CH:12]2[CH2:13][CH2:14]2)[C:7]=1[I:37])=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 807IodineHCID 9869224Ammonium cerium (IV) nitrateHCID 15131404Ethyl 3-cyclopropyl-1-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 58542506HCID 58542506, compoundYield 103.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 500 mg (2.57 mmol) of ethyl-3-cyclopropyl-1-methyl-1H-pyrazole-5-carboxylate (prepared from ethyl-3-cyclopropyl-1H-pyrazole-5-carboxylate in accordance with Bioorg. Med. Chem. Lett. 1996, 6, 1819-1824) in 5 ml of acetonitrile is admixed with 706 mg (1.28 mmol) of ammonium cerium(IV) nitrate and 392 mg (1.53 mmol) of iodine and heated under reflux for three hours and afterstirred overnight at room temperature. The reaction mixture is diluted with water and ethyl acetate, and the organic phase is washed with saturated sodium thiosulphate solution, dried over sodium sulphate, filtered and concentrated by evaporation in vacuo. Chromatographic purification gives 506 mg of ethyl-3-cyclopropyl-4-iodo-1-methyl-1H-pyrazole-5-carboxylate (66%).

Workup

  1. temperatureheated
  2. washthe organic phase is washed with saturated sodium thiosulphate solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation in vacuo
  6. customChromatographic purification

Sources & evidence

ORD record
ord-b7067cd59f554b53a221b718ade48371
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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