Trimethylsilylacetylene → HCID 86717323, compound

HRID 588628Notes

Reaction equation

HRID 588628 reaction equation
I[C:2]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[NH:7][C:8](=[O:10])[CH3:9].[C:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])#[CH:19]>CN(C=O)C.C(N(CC)CC)C.C(OCC)(=O)C.O.[Cu](I)I.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>[CH3:11][N:5]1[C:6]([NH:7][C:8](=[O:10])[CH3:9])=[C:2]([C:19]#[C:18][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4]1

Participants

9

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 86717324HCID 86717324, compound

Product 1

HCID 86717323HCID 86717323, compoundYield 49.2%

Reagents, catalysts & solvents 6

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Nitrogen was bubbled through a mixture of N-(4-iodo-1-methyl-3-phenyl-1H-pyrazol-5-yl)acetamide (5 g, 15 mmol) in DMF (15 mL) and triethylamine (35 mL) for 15 min. Copper iodide (0.56 g, 3.0 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.53 g, 0.75 mmol) and ethynyltrimethylsilane (3.0 g, 30 mmol) were added and the reaction mixture was stirred in a sealed tube at 90° C. under nitrogen for 3 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and water. The organic phase was washed with water and brine, dried (phase separation cartridge) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 5:1 to 10:3) yielding the title compound as a solid (2.3 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic phase was washed with water and brine
  3. customdried
  4. custom(phase separation cartridge)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 5:1 to 10:3)

Sources & evidence

ORD record
ord-ff153acea44d40d79c5d825596921682
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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