Tributylvinyltin → HCID 21188073, compound

HRID 1383610Notes

Reaction equation

HRID 1383610 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]([CH3:19])=[N:14]1.[CH:20]([Sn](CCCC)(CCCC)CCCC)=[CH2:21]>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:20]=[CH2:21])[C:15]([CH3:19])=[N:14]1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 21188047HCID 21188047, compound

Product 1

HCID 21188073HCID 21188073, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)4-iodo-3-methylpyrazole (2.06 g) in dimethylformamide (25 ml) was added tetrakis(triphenylphosphine)palladium(0) (0.1 g) and vinyltri-n-butyltin (2 ml). The mixture was heated at 70° C. for 2 hours. The reaction mixture was eyaporated and then partitioned between water and ether. The aqueous layer was separated and extracted twice with ether. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatigraphy on silica gel eluted with hexane: ether (9:1). Combination and evaporation of appropriate fractions gave a yellow solid which was further purified by reverse phase high performance chromatography on C18 silica eluted with acetonitrile: methanol: water (40:10:50). Combination and evaporation of appropriate fractions gave the title compound as a white solid, m.p.68.1-68.7° C.

Workup

  1. custompartitioned between water and ether
  2. customThe aqueous layer was separated
  3. extractionextracted twice with ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by column chromatigraphy on silica gel
  8. washeluted with hexane: ether (9:1)
  9. customCombination and evaporation of appropriate fractions
  10. customgave a yellow solid which
  11. customwas further purified by reverse phase high performance chromatography on C18 silica
  12. washeluted with acetonitrile: methanol: water (40:10:50)
  13. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-d819706418a04b4bad6b4305b0f39c5c
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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