Reaktion #556868

Reaktionsgleichung

Cs2CO3

4-Bromo-2-methoxypyridine

(6-(trifluoromethyl)pyridin-3-yl)methanol

3,4,7,8-tetramethylphenanthroline

→

title compound

Ausbeute 72.4%

2-Methoxy-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridine

Ausbeute 72.4%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux under a nitrogen atmosphere for 16 h
3. 3
   TemperaturUpon cooling the mixture
4. 4
   Sonstigewas purified by flash column chromatography (silica gel, hexanes/EtOAc, 1:0 to 1:1)

Vorschrift

4-Bromo-2-methoxypyridine (3.06 g, 16.2 mmol), (6-(trifluoromethyl)pyridin-3-yl)methanol (2.74 g, 15.5 mmol), 3,4,7,8-tetramethylphenanthroline (0.36 g, 0.15 mmol), CuI (0.14 g, 0.74 mmol) and Cs2CO3 (7.57 g, 23.2 mmol) were combined in toluene (15 mL) and heated to reflux under a nitrogen atmosphere for 16 h. Upon cooling the mixture was purified by flash column chromatography (silica gel, hexanes/EtOAc, 1:0 to 1:1) to provide the title compound (3.19 g, 72%) as a red oil: 1H NMR (300 MHz, CDCl3) δ 8.78 (s, 1H), 8.02 (d, J=5.9 Hz, 1H), 7.95 (d, J=8.1 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 6.55 (dd, J=5.9, 2.2 Hz, 1H), 6.26 (d, J=2.2 Hz, 1H), 5.16 (s, 2H), 3.93 (s, 3H).

Quelle