Reaktion #1558876

Reaktionsgleichung

5-((2-bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde

DMF

→

3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)picolinonitrile

Ausbeute 84.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solid was filtered off
2. 2
   Einengenthe filtrate was concentrated to dryness
3. 3
   SonstigeThe crude was purified on silica gel using
4. 4
   workup.ADDITIONa mixture of EtOAc and hexanes as eluent

Vorschrift

To a mixture of 5-((2-bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (100 mg, 0.31 mmol, 1 equiv), Zn (CN)2 (71 mg, 0.62 mmol, 2.0 equiv), Pd(PPh3)4 (72 mg, 0.06 mmol, 0.2 equiv) in a 5 mL microwave tube was added DMF (2 mL). The mixture was heated 15 min at 125° C. in a microwave reactor. The solid was filtered off and the filtrate was concentrated to dryness. The crude was purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)picolinonitrile (71 mg, 84%) as a white solid. 1H NMR (400 MHz; CDCl3) δ=10.54 (s, 1H), 8.86 (d, 1H), 8.22 (s, 1H), 8.20 (d, 1H), 7.74 (dd, 1H), 6.37 (s, 1H) 5.52 (s, 2H), 4.04 (s, 3H). LRMS (M+H+) m/z 270.1.

Quelle