Reaktion #80918

Reaktionsgleichung

2-amino-5-ethynyl-6-methylbenzonitrile

4-trifluoromethylphenyl iodide

triethylamine

→

2-amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile

Ausbeute 72.7%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter this time the reaction mixture was concentrated under reduced pressure to a residue
2. 2
   SonstigeThe residue was partitioned between ethyl acetate and aqueous 1N hydrochloric acid
3. 3
   FiltrationThe two-layered mixture was filtered
4. 4
   Sonstigeto remove a solid
5. 5
   SonstigeThe aqueous layer and the organic layer were separated
6. 6
   Waschenthe aqueous layer was washed with ethyl acetate
7. 7
   WaschenThe ethyl acetate wash
8. 8
   Waschenthe combination was washed with an aqueous solution of 10% lithium chloride
9. 9
   TrocknenThe organic layer was dried with magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    EinengenThe filtrate was concentrated under reduced pressure to a residue
12. 12
    SonstigeThe residue was triturated with methylene chloride
13. 13
    Filtrationfiltered
14. 14
    WaschenElution
15. 15
    Einengenconcentrated under reduced pressure

Vorschrift

A solution of 3.5 grams (0.022 mole) of 2-amino-5-ethynyl-6-methylbenzonitrile, 8.4 grams (0.031 mole) of 4-trifluoromethylphenyl iodide, 10.7 grams (0.077 mole) of triethylamine, 0.5 gram (catalyst) of bis(triphenylphosphine)palladium(II) chloride, and 0.5 gram (catalyst) of copper(I) iodide in 100 mL of acetonitrile was stirred at ambient temperature for about 18 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was partitioned between ethyl acetate and aqueous 1N hydrochloric acid. The two-layered mixture was filtered to remove a solid. The aqueous layer and the organic layer were separated, and the aqueous layer was washed with ethyl acetate. The ethyl acetate wash was combined with the organic layer, and the combination was washed with an aqueous solution of 10% lithium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was triturated with methylene chloride and filtered. The filtrate was subjected to column chromatography on silica gel. Elution was accomplished using methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 4.8 grams of 2-amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile, mp 136°-138° C. The NMR spectrum was consistent with the proposed structure.

Quelle