Reaktion #1017940

Reaktionsgleichung

4-bromo-2-methoxypyridine

4-methylthiophenyl boronic acid

K2CO3

→

white powder

Ausbeute 77.8%

4-(4-(Methylthio)phenyl)pyridin-2(1H)-one

Ausbeute 77.8%

Lösungsmittel

DMSO

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed under reduced pressure for 25 min
2. 2
   TemperaturThe suspension was cooled
3. 3
   workup.ADDITIONH2O was added
4. 4
   Filtrationthe suspension was filtered
5. 5
   Sonstigeto afford a light colored solid

Vorschrift

A suspension of 4-bromo-2-methoxypyridine (1.225 g, 6.511 mmol), 4-methylthiophenyl boronic acid (2.188 g, 13.02 mmol), PdCl2(dppf) (531 mg, 0.651 mmol) and K2CO3 (1.797 g, 13.02 mmol) in DMSO (10 mL) was degassed under reduced pressure for 25 min. The suspension was put under N2 and stirred at 95° C. for 16 h. The suspension was cooled, H2O was added, and the suspension was filtered to afford a light colored solid. Flash chromatography (silica gel, hexanes/(1:1 EtOAc/hexanes), 100:0 to 0:100) afforded 1.10 g of a white powder. The white powder was diluted with concentrated HCl solution (50 mL) and stirred at reflux for 24 h. The reaction was cooled and concentrated under reduced pressure. The residue was neutralized with saturated NaHCO3 solution, and the solid was collected by filtration. The solid was washed with H2O to afford the title compound (1.103 g, 71%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 7.65 (d, J=8.4 Hz, 2H), 7.43 (d, J=6.9 Hz, 1H), 7.34 (d, J=8.4 Hz, 2H), 6.57 (d, J=1.7 Hz, 1H), 6.50 (dd, J=6.9, 1.7 Hz, 1H), 3.34 (s, 3H).

Quelle