Reacción #2487463

Ecuación de reacción

Water

sodium hydrogen carbonate

hydroxylamine hydrochloride

6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile

→

title compound

Rendimiento 99.1%

6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime

Rendimiento 99.1%

Disolventes

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGby stirring at 80° C. overnight
2. 2
   Extracciónfollowed by extraction with ethyl acetate
3. 3
   LavadoThe organic layer was washed with water and saturated brine
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a suspension of hydroxylamine hydrochloride (233 mg) in dimethylsulfoxide (1.7 mL) was added sodium hydrogen carbonate (338 mg), and this mixture was stirred at 50° C. for 1 hour. Subsequently, 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile (114 mg) was added thereto, followed by stirring at 80° C. overnight. Water was added to the reaction mixture, 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 to obtain the title compound (124 mg). 1H-NMR (DMSO-d6) δ ppm: 3.76 (3H, s), 5.51 (2H, s), 5.65 (2H, br s), 6.59 (1H, s), 6.70-6.85 (2H, m), 7.11 (1H, d, J=2.4 Hz), 7.32 (1H, d, J=8.9 Hz), 7.35-7.70 (7H, m), 9.92 (1H, s).

Fuente