反应 #2487481

反应方程式

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

溶剂

methanol

tetrahydrofuran

反应条件

后处理

1. 1
   浓缩The 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
   其他at 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
   萃取followed by extraction with ethyl acetate
8. 8
   洗涤The organic layer was washed with saturated brine
9. 9
   干燥dried over anhydrous magnesium sulfate
10. 10
    浓缩concentrated under reduced pressure
11. 11
    其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

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)+

来源