Reaktion #1558922

Reaktionsgleichung

4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-ol

2-bromo-3-(chloromethyl)pyridine hydrochloride

K2CO3

→

5-((2-bromopyridin-3-yl)methoxy)-4-(1,3-dioxolan-2-yl)-2-methoxypyridine

Ausbeute 66.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled
2. 2
   Filtrationfiltered
3. 3
   Einengenconcentrated
4. 4
   Sonstigepurified on silica gel using
5. 5
   workup.ADDITIONa mixture of EtOAc and hexanes as eluent

Vorschrift

A mixture of 4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-ol (980 mg, 4.97 mmol, 1 eq.), 2-bromo-3-(chloromethyl)pyridine hydrochloride (1.2 g, 4.93 mmol, 1 eq.) and K2CO3 (2.7 g, 19.88 mmol, 4 eq.) in DMF (10.0 mL) was heated at 70° C. for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((2-bromopyridin-3-yl)methoxy)-4-(1,3-dioxolan-2-yl)-2-methoxypyridine (1.21 g, 66%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.26 (dd, J=4.7, 1.9 Hz, 1H), 7.83 (dd, J=7.6, 1.9 Hz, 1H), 7.74 (s, 1H), 7.25 (dd, J=7.6, 4.8 Hz, 1H), 6.86 (s, 1H), 6.10 (s, 1H), 5.09 (s, 2H), 4.07-3.93 (m, 4H), 3.82 (s, 3H). LRMS (MAT) m/z 367.0.

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