Reaktion #1017820

Reaktionsgleichung

4-Bromo-2-methoxypyridine

(E)-phenylvinylboronic acid

K2CO3

→

title compound

Ausbeute 93.0%

(E)-2-Methoxy-4-styrylpyridine

Ausbeute 93.0%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe flask was flushed with nitrogen
2. 2
   TemperaturUpon cooling
3. 3
   workup.ADDITIONthe mixture was diluted with methylene chloride
4. 4
   Waschenwashed with 5% lithium chloride solution (5×)
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated
7. 7
   Sonstigethe residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate, 97:3 to 75:25)

Vorschrift

4-Bromo-2-methoxypyridine (1.85 g, 9.84 mmol), (E)-phenylvinylboronic acid (4.3 g, 30 mmol), K2CO3 (4.0 g, 30 mmol) and PdCl2(dppf) (400 mg, 0.5 mmol) were stirred in DMSO (15 mL) under vacuum for 30 min. The flask was flushed with nitrogen and the mixture was heated to 90° C. for 30 min. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5×), dried, concentrated, and the residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate, 97:3 to 75:25) to provide the title compound (1.93 g, 93%) as an orange oil: 1H NMR (300 MHz, CDCl3) δ 8.12 (d, J=5.2 Hz, 1H), 7.51 (m, 2H), 7.40-7.22 (m, 4H), 7.02-6.94 (m, 2H), 6.78 (s, 1H), 3.95 (s, 3H).

Quelle