反应 #2487482

反应方程式

water

6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime

1,1′-thiocarbonyldiimidazole

→

title compound

3-[6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridin-2-yl]-4,5-dihydro-1,2,4-thiadiazol-5-one

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   萃取followed by extraction with ethyl acetate
2. 2
   洗涤The organic layer was washed with water
3. 3
   干燥dried over anhydrous magnesium sulfate
4. 4
   浓缩concentrated under reduced pressure
5. 5
   workup.ADDITIONTo the residue was added tetrahydrofuran (2 mL), and subsequently boron trifluoride ethyl ether complex (0.21 mL)
6. 6
   workup.ADDITIONwas added
7. 7
   温度under ice-cooling
8. 8
   workup.STIRRINGThe mixture was stirred at room temperature for 3 days
9. 9
   workup.ADDITIONTo the reaction mixture was added water
10. 10
    萃取followed by extraction with ethyl acetate
11. 11
    洗涤The organic layer was washed with 1 mol/L hydrochloric acid and water successively
12. 12
    干燥dried over anhydrous magnesium sulfate
13. 13
    浓缩concentrated under reduced pressure
14. 14
    其他The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol)

实验过程

To a solution of 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime (123 mg) in tetrahydrofuran (2 mL) was added 1,1′-thiocarbonyldiimidazole (71 mg). This mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the residue was added tetrahydrofuran (2 mL), and subsequently boron trifluoride ethyl ether complex (0.21 mL) was added thereto under ice-cooling. The mixture was stirred at room temperature for 3 days. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid and water successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol) to obtain the title compound (24 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.55 (2H, s), 6.45-6.55 (1H, m), 6.60-6.70 (1H, m), 6.77 (1H, dd, J=2.5, 8.9 Hz), 7.14 (1H, d, J=2.5 Hz), 7.28 (1H, d, J=8.9 Hz), 7.35-7.60 (5H, m), 7.75-7.95 (2H, m), 13.35 (1H, br s). ESI-MS (m/z): 415 (M+H)+

来源