Triethylamine → 2-Methyl-3-((trimethylsilyl)ethynyl)pyridine

HRID 31674Notes

Reaction equation

HRID 31674 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([CH3:13])=[N:9][CH:10]=[CH:11][CH:12]=1)(=O)=O.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18].C(N(CC)CC)C>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[CH3:13][C:8]1[C:7]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 107764652-Methylpyridin-3-yl trifluoromethanesulfonate

Product 1

HCID 597925602-Methyl-3-((trimethylsilyl)ethynyl)pyridineYield 84.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

First, 2-methylpyridin-3-yl trifluoromethanesulfonate (34.3 g, 142 mmol), trimethylsilylacetylene (30 ml, 212 mmol), bis(triphenylphosphine)palladium (II) chloride (10.0 g, 14.2 mmol), and copper (I) iodide (2.75 g, 14.4 mmol) were dissolved in N,N-dimethyl formamide (150 ml). Thereafter, triethylamine (43 ml, 309 mmol) was added in a nitrogen atmosphere at room temperature to the mixture. The mixture was then stirred for 3 hours (exothermic reaction took place). The reaction mixture was separated by ethyl acetate and a saturated aqueous ammonium chloride solution and insoluble substance was removed by filtration. The organic layer of the filtrate was washed twice with a saturated aqueous ammonium chloride solution, dried over anhydrous magnesium sulfate, filtrated and concentrated to obtain the title compound (22.6 g, yield: 84.1%) as brown oil.

Workup

  1. custom(exothermic reaction took place)
  2. customThe reaction mixture was separated by ethyl acetate
  3. customa saturated aqueous ammonium chloride solution and insoluble substance was removed by filtration
  4. washThe organic layer of the filtrate was washed twice with a saturated aqueous ammonium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-14f8cb66d4b1424fbd3ad21b9d5df339
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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