反应详情

温度

125 °C

2-Pyridinecarboxaldehyde (4.76 mL, 50 mmol) and tosylmethyl isocyanide (9.76 g, 50 mmol) were suspended in ethanol (150 mL) at room temperature. A catalytic amount of potassium cyanide (0.33 g) was added and the resulting mixture was stirred for 45 min. The mixture became homogeneous after 5 min. of stirring and then a white suspension appeared. The solid material was collected by filtration and rinsed with diethyl ether. After drying under vacuum the solid was transferred to a sealed tube. A 2M solution of ammonia in methanol (20 mL) was added and the tube was sealed and heated at 125° C. for 24 h. The dark reaction mixture was cooled to room temperature and the solvents removed in vacuo. The residue was purified by silica gel chromatography (20-100% EtOAc/Hexane then 0%-50% MeOH/CH2Cl2) to afford 2-(1H-imidazol-4-yl)pyridine as a dark oil. 1H NMR (500 MHz, CD3OD) δ 8.31 (d, 1H), 7.92 (s, 1H), 7.72-7.63 (m, 3H), 7.54 (s, 1H), 7.07 (m, 1H).

1. waitThe mixture became homogeneous after 5 min.
2. stirringof stirring
3. filtrationThe solid material was collected by filtration
4. washrinsed with diethyl ether
5. customAfter drying under vacuum the solid
6. customwas transferred to a sealed tube
7. additionA 2M solution of ammonia in methanol (20 mL) was added
8. customthe tube was sealed
9. customThe dark reaction mixture
10. temperaturewas cooled to room temperature
11. customthe solvents removed in vacuo
12. customThe residue was purified by silica gel chromatography (20-100% EtOAc/Hexane