Trimethylsilylacetylene → HCID 21188087, compound

HRID 1383603Notes

Reaction equation

HRID 1383603 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]([F:22])([F:21])[F:20])[C:3]=1I.[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26]>C(N(CC)CC)C.CN(C)C=O.O.CCOCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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]([F:22])([F:21])[F:20])[C:3]=1[C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24]

Participants

8

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 22618498HCID 22618498, compound

Product 1

HCID 21188087HCID 21188087, compound

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodo-3-trifluoromethylpyrazole (28 g) in triethylamine (120 ml) and dimethylformamide (24 ml) at room temperature was added trimethylsilylacetylene (12 ml), cuprous iodide (0.6 g) and bis(triphenylphosphine)palladium(II) chloride (1.2 g). The mixture was heated under reflux for 4 hours and then left at room temperature overnight. The reaction mixture was diluted with water (500 ml) and ether (500 ml) and filtered. The filtrate's organic layer was separated, dried (MgSO4) and evaporated to give the crude product as an oil which was purified by column chromatography on silica gel eluted with dichloromethane:hexane (1:1). Combination and evaporation of appropriate fractions, followed by recrystallisation from hexane, provided the title compound as a buff solid, m.p. 120-123° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. filtrationfiltered
  4. customThe filtrate's organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give the crude product as an oil which
  8. customwas purified by column chromatography on silica gel
  9. washeluted with dichloromethane:hexane (1:1)
  10. customCombination and evaporation of appropriate fractions
  11. customfollowed by recrystallisation from hexane

Sources & evidence

ORD record
ord-b63a9bef39e04b47a1739b6d654fcb33
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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