반응 #2487466

반응 방정식

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

수율 87.4%

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

수율 87.4%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGby stirring at room temperature for 1 hour
2. 2
   추출followed by extraction with ethyl acetate
3. 3
   세척The organic layer was washed with water and saturated brine
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was recrystallized from ethanol

실험 절차

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).

출처