N-Iodosuccinimide → HCID 22120889, compound

HRID 1108817Notes

Reaction equation

HRID 1108817 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([C:16]#[N:17])[CH:3]=1.IN1[C:23](=O)[CH2:22][CH2:21][C:20]1=[O:25]>C(#N)C>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([C:16]#[N:17])[C:3]=1[C:23]1[O:25][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 22120893HCID 22120893, compound

Product 1

HCID 22120889HCID 22120889, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-methylphenyl)pyrazole (1 g) in acetonitrile (15 ml) at room temperature was added N-iodosuccinimide (0.845 g). Stirring was continued for 10 minutes and the mixture was then evaporated to dryness. The residue was taken up in dioxane (20 ml). Furan-2-boronic acid (0.845 g), tetrakis(triphenylphosphine)palladium(0) (0.35 g) and a solution of potassium carbonate (2.8 g) in water (8 ml) were added. The mixture was heated under reflux for 24 hours, then cooled and partitioned between ether and water. The separated aqueous layer was extracted with ether and the combined ether layers were washed with brine, dried and evaporated. The green oily residue was purified by column chromatography on silica gel eluted with hexane:dichloromethane (1:2). Combination and evaporation of suitable fractions followed by recrystallisation from toluene gave the title compound as a white solid, m.p. 191.5-192.5° C.

Workup

  1. customthe mixture was then evaporated to dryness
  2. additionFuran-2-boronic acid (0.845 g), tetrakis(triphenylphosphine)palladium(0) (0.35 g) and a solution of potassium carbonate (2.8 g) in water (8 ml) were added
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 24 hours
  5. temperaturecooled
  6. custompartitioned between ether and water
  7. extractionThe separated aqueous layer was extracted with ether
  8. washthe combined ether layers were washed with brine
  9. customdried
  10. customevaporated
  11. customThe green oily residue was purified by column chromatography on silica gel
  12. washeluted with hexane:dichloromethane (1:2)
  13. customCombination and evaporation of suitable fractions
  14. customfollowed by recrystallisation from toluene

Sources & evidence

ORD record
ord-80388aeb1e5d4674bcd8aef8ef6caf34
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Reaction notes

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