Tributylvinyltin → HCID 21188093, compound

HRID 1383602Notes

Reaction equation

HRID 1383602 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]([F:22])([F:21])[F:20])=[N:14]1.[CH:23]([Sn](CCCC)(CCCC)CCCC)=[CH2:24]>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:23]=[CH2:24])[C:15]([C:19]([F:22])([F:21])[F:20])=[N:14]1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 21188090HCID 21188090, compound

Product 1

HCID 21188093HCID 21188093, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodo-3-trifluoromethylpyrazole (1 g) in dimethylformamide (5 ml) containing vinyltri-n-butyltin (2 ml) and tetrakis(triphenylphosphine)palladium(0) (0.1 g) was stirred at 75° C. for 3 hours. The reaction mixture was evaporated and then partitioned between water and ether. The organic layer was separated, washed with water (×5), dried (Na2SO4) and evaporated. The residue was crystailised from hexane and further purified by column chromatography on silica gel eluted with ether. 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, followed by recrystallisation from propan-2-ol, gave the title compound as a light yellow solid, m.p.95-98° C.

Workup

  1. customThe reaction mixture was evaporated
  2. custompartitioned between water and ether
  3. customThe organic layer was separated
  4. washwashed with water (×5)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customfurther purified by column chromatography on silica gel
  8. washeluted with ether
  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
  14. customfollowed by recrystallisation from propan-2-ol

Sources & evidence

ORD record
ord-392eba63cfec4b2cb39ec4608f5399a9
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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