Trimethylsilylacetylene → HCID 57983432, compound

HRID 2078318Notes

Reaction equation

HRID 2078318 reaction equation
I[C:2]1[C:3]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:13]([Si:15]([CH3:18])([CH3:17])[CH3:16])#[CH:14]>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][C:8]([C:3]1[C:2]([C:14]#[C:13][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:7][CH:6]=[CH:5][N:4]=1)([CH3:12])[C:9]#[N:10]

Participants

4

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 57983450HCID 57983450, compound

Product 1

HCID 57983432HCID 57983432, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

2-(3-Iodopyridin-2-yl)-2-methylpropanenitrile (1.8 g, 6.6 mmol), cuprous iodide (0.045 mL, 1.3 mmol) and dichlorobis(triphenylphosphine)palladium (II) (0.46 g, 0.66 mmol) were dissolved in TEA (20 mL, 143 mmol). Ethynyltrimethylsilane (4.7 mL, 33 mmol) was added to the reaction mixture, and the reaction mixture was placed under an argon atmosphere. The reaction mixture was stirred and heated at 80° C. After 45 minutes, the reaction was >95% complete as determined by LCMS. The reaction was cooled to room temperature and then filtered through Celite to remove a dark solid. The filtrate was concentrated in vacuo and purified by silica flash chromatography (0-50% EtOAc/hexane) to give the title compound as a light-orange oil (1.6 g, 100%). MS (m/z)=243 (M+H)+. Calculated for C14H18N2Si 242.4.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customto remove a dark solid
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by silica flash chromatography (0-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-bf3e41ba10dd4c84a455fab3765f9fd7
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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