반응 #2487479

반응 방정식

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

수율 100.7%

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

수율 100.7%

용매

acetonitrile

반응 조건

후처리

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

실험 절차

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)+

출처