Réaction #2487481

Équation de réaction

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

Solvants

methanol

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   ConcentrationThe 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
   Autreat 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
   Extractionfollowed by extraction with ethyl acetate
8. 8
   LavageThe organic layer was washed with saturated brine
9. 9
   Séchagedried over anhydrous magnesium sulfate
10. 10
    Concentrationconcentrated under reduced pressure
11. 11
    AutreThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Mode opératoire

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)+

Source