反応 #91313

反応方程式

Methyl 3-bromoisonicotinate

4-fluorobenzylamine

Xantphos

cesium carbonate

→

title compound

収率 88.0%

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

収率 88.0%

溶媒

dioxane

反応条件

後処理

1. 1
   ろ過The mixture was then filtered
2. 2
   洗浄washing with DCM
3. 3
   その他to remove solids
4. 4
   濃縮The solution was concentrated in vacuo
5. 5
   その他purified by silica gel chromatography (20-50% EtOAc/hexanes)

実験手順

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.

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