Reaktion #510418

Reaktionsgleichung

4-(4-bromophenyl)-3,5-diphenyl-4H-1,2,4-triazole

3-pyridineboronic acid

sodium carbonate

→

powdery white solid

Ausbeute 76.0%

3-(4-(3,5-diphenyl-4H-1,2,4-triazol-4-yl)phenyl)pyridine

Ausbeute 76.0%

Lösungsmittel

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 100 mL three-neck flask were put
2. 2
   SonstigeThis mixture was degassed under reduced pressure
3. 3
   workup.ADDITIONAfter the stir, dichloromethane was added to the reacted mixture
4. 4
   Waschenthe suspension was washed with 1M diluted hydrochloric acid
5. 5
   SonstigeThe organic layer and the aqueous layer were separated
6. 6
   workup.ADDITIONMagnesium sulfate was added to the organic layer
7. 7
   Sonstigeto dry the organic layer
8. 8
   FiltrationAfter the drying, this mixture was subjected to suction filtration through Celite (Catalog No. 531-16855, manufactured by Wako Pure Chemical Industries, Ltd.)
9. 9
   Sonstigeto obtain the filtrate
10. 10
    EinengenThe obtained filtrate was concentrated
11. 11
    Sonstigepurified by silica gel column chromatography
12. 12
    EinengenThe obtained fraction was concentrated
13. 13
    Sonstigeto give a solid
14. 14
    SonstigeThe obtained solid was recrystallized with a mixed solvent of ethanol and hexane

Vorschrift

Into a 100 mL three-neck flask were put 2.0 g (5.3 mmol) of 4-(4-bromophenyl)-3,5-diphenyl-4H-1,2,4-triazole, 0.98 g (8.0 mmol) of 3-pyridineboronic acid, and 0.28 g (1.1 mmol) of tetrakis(triphenylphosphine)palladium(0), and 10 mL of 1,2-dimethoxyethane (DME) and 10 mL of a 2M sodium carbonate aqueous solution were added to the mixture. This mixture was degassed under reduced pressure. After that, the air in the flask was replaced with nitrogen. This mixture was stirred at 95° C. for 3 hours. After the stir, dichloromethane was added to the reacted mixture, and the suspension was washed with 1M diluted hydrochloric acid, a saturated sodium hydrogen carbonate solution, and saturated saline. The organic layer and the aqueous layer were separated. Magnesium sulfate was added to the organic layer to dry the organic layer. After the drying, this mixture was subjected to suction filtration through Celite (Catalog No. 531-16855, manufactured by Wako Pure Chemical Industries, Ltd.) to obtain the filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography. For the column chromatography, first toluene and then a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=1:3) were used as developing solvents. The obtained fraction was concentrated to give a solid. The obtained solid was recrystallized with a mixed solvent of ethanol and hexane to give 1.5 g of a powdery white solid, which was the object of the synthesis, at a yield of 76%.

Quelle