4-ethynylpyridin-2-amine

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4-ethynylpyridin-2-amine Basic information
Product Name:4-ethynylpyridin-2-amine
Synonyms:4-ethynylpyridin-2-amine;4-Ethynyl-pyridin-2-ylamine;4-Ethynyl-2-pyridinamine;2-Pyridinamine, 4-ethynyl-
CAS:1094679-27-2
MF:C7H6N2
MW:118.14
EINECS:
Product Categories:
Mol File:1094679-27-2.mol
4-ethynylpyridin-2-amine Structure
4-ethynylpyridin-2-amine Chemical Properties
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
AppearanceLight brown to brown Solid
Safety Information
MSDS Information
4-ethynylpyridin-2-amine Usage And Synthesis
Synthesis
2-Amino-4-bromopyridine

84249-14-9

Trimethylsilylacetylene

1066-54-2

4-ethynylpyridin-2-amine

1094679-27-2

Using 2-amino-4-bromopyridine (400 mg, 2.31 mmol) and trimethylsilylacetylene (0.38 mL, 2.77 mmol), bis(benzylcarbonitrile)dichloropalladium (II) was prepared in the presence of cesium carbonate (39.1 mg, 0.12 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylx-ton (69.4 mg, 0.12 mmol). Palladium(II) chloride (46.0 mg, 0.12 mmol) was dissolved in DMF (5 mL). Subsequently, triethylamine (2 mL) was added and the reaction mixture was stirred at 50 °C in an oil bath for 2 hours. Upon completion of the reaction, THF (3 mL) and tetrabutylammonium fluoride (2.77 mL) were added, the solvent was concentrated under reduced pressure, and then the reaction was continued for 30 min at room temperature. Finally, the solvent was evaporated and the residue was purified by silica gel column chromatography using a solvent mixture of chloroform and methanol (1:50) as eluent to afford the target product 4-ethynylpyridin-2-amine (90.1 mg, 33% yield).

References[1] Patent: JP2015/221769, 2015, A. Location in patent: Paragraph 0031; 0033
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