Tributylvinyltin → HCID 10947997, compound

HRID 377648Notes

Reaction equation

HRID 377648 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1I.[CH:22]([Sn](CCCC)(CCCC)CCCC)=[CH2:23]>CN(C)C=O.O>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[CH:22]=[CH2:23]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 10947997HCID 10947997, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (2 g) in dimethylformamide (10 ml) at room temperature was added vinyltri-n-butyl tin (4.25 g) and tetra-kis-triphenylphosphinepalladium(0) (0.3 g). The mixture was heated at 75° C. for one hour and then cooled and left at room temperature for 60 hours. The reaction mixture was diluted with water and extracted with ether. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to give the crude product as a black oil (6 g) which was purified by column chromatography on silica gel (200 g) eluted with dichloromethane:hexane (1:1). Combination and evaporation of appropriate fractions gave the title compound as a buff solid, m.p. 186-70° C.

Workup

  1. temperaturecooled
  2. extractionextracted with ether
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give the crude product as a black oil (6 g) which
  8. customwas purified by column chromatography on silica gel (200 g)
  9. washeluted with dichloromethane:hexane (1:1)
  10. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-16990b5ad85d4454a1a6d5d4c98add00
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

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