反应 #2487466

反应方程式

hydrochloric acid

1,1′-carbonyldiimidazole

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

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

1,1′-carbonyldiimidazole

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

→

title compound

收率 87.4%

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

收率 87.4%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   workup.STIRRINGby stirring at room temperature for 1 hour
2. 2
   萃取followed by extraction with ethyl acetate
3. 3
   洗涤The organic layer was washed with water and saturated brine
4. 4
   干燥dried over anhydrous magnesium sulfate
5. 5
   浓缩concentrated under reduced pressure
6. 6
   其他The residue was recrystallized from ethanol

实验过程

To a solution of 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime (124 mg) in tetrahydrofuran (1.7 mL) were added 1,1′-carbonyldiimidazole (57 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (53 μL). This mixture was stirred at room temperature for 2 hours. To the reaction mixture were added 1,1′-carbonyldiimidazole (27 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (25 μL), followed by stirring at room temperature for 1 hour. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from ethanol to obtain the title compound (116 mg). 1H-NMR (DMSO-d6) δ ppm: 3.78 (3H, s), 5.55 (2H, s), 6.55-6.70 (2H, m), 6.77 (1H, dd, J=2.4, 8.9 Hz), 7.15 (1H, d, J=2.4 Hz), 7.26 (1H, d, J=8.9 Hz), 7.35-7.55 (5H, m), 7.75-7.90 (2H, m), 13.07 (1H, br s).

来源