反应 #2487479

反应方程式

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

收率 100.7%

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

收率 100.7%

溶剂

acetonitrile

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 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively
3. 3
   干燥dried over anhydrous sodium sulfate
4. 4
   浓缩concentrated under reduced pressure
5. 5
   其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-methanol)

实验过程

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)+

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