Tributylvinyltin → HCID 21188130, compound

HRID 1383607Notes

Reaction equation

HRID 1383607 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([CH3:18])=[C:16](I)[C:15]([CH3:20])=[N:14]1.[CH:21]([Sn](CCCC)(CCCC)CCCC)=[CH2:22]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([CH3:18])=[C:16]([CH:21]=[CH2:22])[C:15]([CH3:20])=[N:14]1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 21188049HCID 21188049, compound

Product 1

HCID 21188130HCID 21188130, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3,5-dimethyl4-iodopyrazole (1 g) in dimethylformamide (10 ml) containing yinyltri-n-butyltin (2 ml) and tetrakis(triphenylphosphine)palladium(0) (0.1 g) was stirred at 75° C. for 2 hours then left overnight at room temperature. The mixture was again heated at 75° C. for 2 hours then vinyltri-n-butyltin (2 ml) was added and the mixture heated at 75° C. for 2 hours. Tetrakis(triphenylphosphine)palladium(0) (0.1 g) was added and heating continued for a further 2 hours. The reaction mixture was evaporated and the residue partitioned between water and dichloromethane. The organic layer was separated, washed with water (×2), then brine, dried (Na2SO4) and evaporated. The residue was adsorbed onto silica gel (20 g) and purified by column chromatography on silica gel (150 g) eluted with hexane, then hexane with increasing amounts of dichloromethane and finally dichloromethane. Combination and evaporation of suitable fractions provided the title compound as yellow oil.

Workup

  1. waitthen left overnight at room temperature
  2. temperatureThe mixture was again heated at 75° C. for 2 hours
  3. temperaturethe mixture heated at 75° C. for 2 hours
  4. temperatureheating
  5. waitcontinued for a further 2 hours
  6. customThe reaction mixture was evaporated
  7. customthe residue partitioned between water and dichloromethane
  8. customThe organic layer was separated
  9. washwashed with water (×2)
  10. dry with materialbrine, dried (Na2SO4)
  11. customevaporated
  12. custompurified by column chromatography on silica gel (150 g)
  13. washeluted with hexane
  14. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-b4960cde2c5443c2839f90176e57d5a0
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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