Triethylamine → HCID 58047434, compound

HRID 1888738Notes

Reaction equation

HRID 1888738 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=1.[CH2:11](N(CC)CC)[CH3:12].C[Si](C#C)(C)C.C(=O)([O-])O.[Na+]>C1COCC1.[Cu]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.O>[CH2:9]([O:8][C:5]1[CH:4]=[CH:3][C:2]([C:11]#[CH:12])=[CH:7][N:6]=1)[CH3:10]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 516892Sodium BicarbonateHCID 8172375-Bromo-2-ethoxypyridine

Product 1

HCID 58047434HCID 58047434, compoundYield 19%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-2-ethoxypyridine (5.00 g, 24.8 mmol) in THF (50 mL)-triethylamine (25 mL) were added trimethylsilylacetylene (5.3 mL, 37.2 mmol), copper(I) iodide (237 mg, 1.24 mmol) and bis(triphenylphosphine)palladium(II) chloride (870 mg, 1.24 mmol), and the mixture was stirred under an argon stream at 60° C. for 1 hr. Water was added to the reaction mixture, the mixture was extracted twice with hexane, and the combined organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=19:1) to give an oil. To a solution of the oil in THF (50 mL) was added 1 M tetrabutylammonium fluoride THF solution (26.0 mL, 26.0 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted twice with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=19:1) to give the title compound (690 mg, yield 19%) as an oil.

Workup

  1. extractionthe mixture was extracted twice with hexane
  2. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=19:1)
  5. customto give an oil
  6. stirringthe mixture was stirred at room temperature for 30 min
  7. extractionthe mixture was extracted twice with diethyl ether
  8. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-c34510a1d3b14464856db2d1e5d52e49
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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