Reaktion #91313

Reaktionsgleichung

Methyl 3-bromoisonicotinate

4-fluorobenzylamine

Xantphos

cesium carbonate

→

title compound

Ausbeute 88.0%

methyl 3-[(4-fluorobenzyl)amino]pyridine-4-carboxylate

Ausbeute 88.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was then filtered
2. 2
   Waschenwashing with DCM
3. 3
   Sonstigeto remove solids
4. 4
   EinengenThe solution was concentrated in vacuo
5. 5
   Sonstigepurified by silica gel chromatography (20-50% EtOAc/hexanes)

Vorschrift

Methyl 3-bromoisonicotinate (220 mg, 1.02 mmol), 4-fluorobenzylamine (132 μL, 1.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (47 mg, 0.051 mmol), Xantphos (89 mg, 0.153 mmol), and cesium carbonate (500 mg, 1.53 mmol) were combined in dioxane (4 mL) under N2 in a sealed microwave tube. The reaction mixture was heated at 116° C. in a microwave for 1 h. The mixture was then filtered, washing with DCM, to remove solids. The solution was concentrated in vacuo and purified by silica gel chromatography (20-50% EtOAc/hexanes) to give 228 mg (88%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.18 (s, 1H), 7.93 (d, 1H, J=5.0 Hz), 7.79 (br s, 1H), 7.63 (d, 1H, J=5.0 Hz), 7.27-7.34 (m, 2H), 7.03 (t, 2H, J=8.6 Hz), 4.47 (d, 2H, J=5.6 Hz), 3.89 (s, 3H). [M+H] calc'd for C14H13FN2O2, 261. found 261.

Quelle