Réaction #2487479

Équation de réaction

hydrochloric acid

1,1′-thiocarbonyldiimidazole

6-[2-(2,5-difluorophenyl)-5-methoxyindol-1-ylmethyl]pyridine-2-carboxamidoxime

1,8-diazabicyclo[5.4.0]undec-7-ene

→

title compound

Rendement 100.7%

3-{6-[2-(2,5-Difluorophenyl)-5-methoxyindol-1-ylmethyl]pyridin-2-yl}-4,5-dihydro-1,2,4-oxadiazol-5-thione

Rendement 100.7%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Extractionfollowed by extraction with ethyl acetate
2. 2
   LavageThe organic layer was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutreThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-methanol)

Mode opératoire

To a suspension of 6-[2-(2,5-difluorophenyl)-5-methoxyindol-1-ylmethyl]pyridine-2-carboxamidoxime (63 mg) in acetonitrile (1.54 mL) were successively added 1,1′-thiocarbonyldiimidazole (41 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.092 mL), followed by stirring at room temperature for 3 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-methanol) to obtain the title compound (70 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.41 (2H, s), 6.50-6.60 (1H, m), 6.67 (1H, s), 6.80 (1H, dd, J=2.4, 9.0 Hz), 7.15 (1H, d, J=2.4 Hz), 7.25-7.45 (3H, m), 7.50-7.60 (1H, m), 7.65-7.80 (2H, m). ESI-MS (m/z): 451 (M+H)+

Source