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

Participants

Reaction Steps

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).

Provenance & Evidence