Trimethylsilylacetylene → HCID 21188103, compound

HRID 1274340Notes

Reaction equation

HRID 1274340 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.[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24]>C(N(CC)CC)C.CN(C)C=O.O.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]#[N:20])[C:3]=1[C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22]

Participants

7

Reactant 2

HCID 66111Trimethylsilylacetylene2×HCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 21188103HCID 21188103, compound

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (6.96 g, crude from Preparation A1) in triethylamine (30 ml) and dimethylformamide (6 ml) at room temperature was added trimethylsilylacetylene (3 ml), cuprous iodide (150 mg) and bis(triphenylphosphine)palladium(II) chloride (300 mg). The mixture was heated at 50-60° C. for one hour, trimethylsilylacetylene (0.3 ml) was then added and stirring and heating continued for a further period of 30 minutes. The cooled reaction mixture was diluted with water (250 ml) extracted with ether (250 ml). The organic layer was separated (aided by the addition of brine). The aqueous layer was re-extracted with ether (250 ml). The combined ether extracts were dried (MgSO4) and evaporated to give the crude product as a gum (4.67 g).

Workup

  1. temperatureheating
  2. customThe cooled reaction mixture
  3. extractionextracted with ether (250 ml)
  4. customThe organic layer was separated (
  5. additionaided by the addition of brine)
  6. extractionThe aqueous layer was re-extracted with ether (250 ml)
  7. dry with materialThe combined ether extracts were dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-d3fae4ecdbaf4be7a4e0a7957879e29f
Source dataset
uspto-grants-2000_12
Patent number
US06156782

Reaction notes

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