Réaction #2487482

Équation de réaction

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

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Extractionfollowed by extraction with ethyl acetate
2. 2
   LavageThe organic layer was washed with water
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated 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
   Températureunder 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
    Extractionfollowed by extraction with ethyl acetate
11. 11
    LavageThe organic layer was washed with 1 mol/L hydrochloric acid and water successively
12. 12
    Séchagedried over anhydrous magnesium sulfate
13. 13
    Concentrationconcentrated under reduced pressure
14. 14
    AutreThe residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol)

Mode opératoire

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)+

Source