반응 #2487481

반응 방정식

methyl 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate

hydrazine monohydrate

→

title compound

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

용매

methanol

tetrahydrofuran

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in tetrahydrofuran (1 mL)
3. 3
   workup.ADDITION1,1′-carbonyldiimidazole (46 mg) was added
4. 4
   기타at room temperature
5. 5
   workup.STIRRINGThe mixture was stirred at room temperature for 2 hours
6. 6
   workup.ADDITIONTo the reaction mixture was added 1 mol/L hydrochloric acid
7. 7
   추출followed by extraction with ethyl acetate
8. 8
   세척The organic layer was washed with saturated brine
9. 9
   건조dried over anhydrous magnesium sulfate
10. 10
    농축concentrated under reduced pressure
11. 11
    기타The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

실험 절차

To a solution of methyl 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate (70 mg) in methanol (1.2 mL) and tetrahydrofuran (0.4 mL) was added hydrazine monohydrate (0.091 mL). This mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (1 mL), and then 1,1′-carbonyldiimidazole (46 mg) was added thereto at room temperature. The mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (48 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.52 (2H, s), 6.62 (1H, s), 6.65-6.80 (2H, m), 7.13 (1H, d, J=2.5 Hz), 7.25 (1H, d, J=8.9 Hz), 7.35-7.50 (3H, m), 7.55-7.65 (2H, m), 7.75 (1H, d, J=7.9 Hz), 7.85 (1H, t, J=7.9 Hz), 12.78 (1H, br s). ESI-MS (m/z): 399 (M+H)+

출처