反应 #2320159

反应方程式

potassium fluoride

2-chloro-3-cyanopyridine

3-thiopheneboronic acid

→

title compound

收率 56.0%

2-thiophen-3-ylnicotinonitrile

收率 56.0%

反应条件

后处理

1. 1
   其他To an oven-dried, N2-purged
2. 2
   workup.ADDITION50 mL, round-bottomed flask containing a magnetic stir bar
3. 3
   其他The flask was sealed with a septum
4. 4
   其他purged with dry N2 atmosphere
5. 5
   workup.ADDITIONAnhydrous dioxane (4 mL) was added via syringe
6. 6
   温度After cooling to room temperature
7. 7
   workup.ADDITIONethyl acetate (15 mL) was added
8. 8
   过滤the mixture was filtered through a pad of silica
9. 9
   浓缩The filtrate was concentrated by rotary evaporation
10. 10
    其他to give a brown oil
11. 11
    其他The product was purified by recrystallization from ethyl acetate/hexanes

实验过程

To an oven-dried, N2-purged, 50 mL, round-bottomed flask containing a magnetic stir bar were added potassium fluoride (767 mg, 13.2 mmol), bis(tri-t-butylphosphine)palladium (51.0 mg, 0.10 mmol), tris(dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol), 2-chloro-3-cyanopyridine (559 mg, 4.00 mmol), and 3-thiopheneboronic acid (819 mg, 6.4 mmol). The flask was sealed with a septum and purged with dry N2 atmosphere. Anhydrous dioxane (4 mL) was added via syringe. The reaction mixture was heated to ˜90° C. in an oil bath for 18 hours. After cooling to room temperature, ethyl acetate (15 mL) was added and the mixture was filtered through a pad of silica. The filtrate was concentrated by rotary evaporation to give a brown oil. The product was purified by recrystallization from ethyl acetate/hexanes to give 417 mg (56%) of the title compound. MS (ESI−) m/z 186.9 (M+H)+; 1H NMR (CDCl3) δ 7.30 (7.8, 4.7 Hz, 1H), 7.44 (dd, J=5.3, 2.9 Hz, 1H), 7.88 (dd, J=5.1, 1.4 Hz, 1H), 8.03 (dd, J=8.0, 1.9 Hz, 1H), 8.29 (dd, J=3.0, 1.4 Hz, 1H), 8.82 (dd, J=4.7, 1.7 Hz, 1H).

来源