Reaktion #2307434

Reaktionsgleichung

5-bromo-2-iodopyridine

toluene

→

title compound

Ausbeute 84.0%

5-Bromo-2-o-tolylpyridine

Ausbeute 84.0%

Lösungsmittel

sodium carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo an argon-purged
2. 2
   SonstigeThe reaction mixture was purged
3. 3
   Sonstigeevacuated with argon twice more
4. 4
   Temperaturto reflux under argon for 15 h
5. 5
   TemperaturThe reaction was cooled
6. 6
   Sonstigepartitioned between water and EtOAc
7. 7
   SonstigeThe layers were separated
8. 8
   Extraktionthe aqueous layer extracted once more with EtOAc
9. 9
   Trocknendried over magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated
12. 12
    Sonstigedried in vacuo
13. 13
    Sonstigeto give the crude product as an orange oil
14. 14
    SonstigePurification by silica gel chromatography (7:3 CH2Cl2/hexanes)

Vorschrift

To an argon-purged and evacuated slurry of 910 mg (3.21 mmol) of 5-bromo-2-iodopyridine and 436 mg (3.21 mmol, 1.0 eq.) of 2-o-tolylboronic acid in 8 mL of toluene and 3.2 mL of 2 M aqueous sodium carbonate, was added 36 mg (0.032 mmol, 0.01 eq) of tetrakis(triphenylphosphine) palladium. The reaction mixture was purged and evacuated with argon twice more and then set to reflux under argon for 15 h. The reaction was cooled and partitioned between water and EtOAc. The layers were separated, and the aqueous layer extracted once more with EtOAc. The organic extracts were combined, dried over magnesium sulfate, filtered, concentrated and dried in vacuo to give the crude product as an orange oil. Purification by silica gel chromatography (7:3 CH2Cl2/hexanes) provided the title compound as a yellow oil, 666 mg, 84% yield.

Quelle