Tributylvinyltin → HCID 21188121, compound

HRID 1383617Notes

Reaction equation

HRID 1383617 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[CH:17]=[C:16](I)[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:14]1.[CH:25]([Sn](CCCC)(CCCC)CCCC)=[CH2:26]>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[CH:17]=[C:16]([CH:25]=[CH2:26])[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:14]1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 21188064HCID 21188064, compound

Product 1

HCID 21188121HCID 21188121, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodo-3-phenylpyrazole (1 g) in dimethylformamide (12 ml) was added tetrakis(triphenylphosphine)palladium(0) (0.07 g) and the mixture stirred at room temperature for 10 minutes. Vinyltri-n-butyltin (1.8 ml) was added and the mixture heated at 70° C. for 6 hours and then left at room temperature overnight. The reaction mixture was evaporated and then partitioned between water (50 ml) and dichloromethane (50 ml). The organic layer was separated, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel eluted with hexane containing increasing amounts of ethyl acetate. Appropriate fractions were combined and evaporated and their residue was further purified by column chromatography on silica gel eluted with hexane containing amounts of ether. Combination and evaporation of appropriate fractions gave the title compound as a yellow oil.

Workup

  1. temperaturethe mixture heated at 70° C. for 6 hours
  2. waitleft at room temperature overnight
  3. customThe reaction mixture was evaporated
  4. custompartitioned between water (50 ml) and dichloromethane (50 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluted with hexane containing
  10. temperatureincreasing amounts of ethyl acetate
  11. customevaporated
  12. customtheir residue was further purified by column chromatography on silica gel
  13. washeluted with hexane containing amounts of ether
  14. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-79a3954c9618449fb2705393b0950584
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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