Reacción #2487465

Ecuación de reacción

hydrochloric acid

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

isopropyl alcohol

sodium azide

→

title compound

Rendimiento 82.2%

5-Methoxy-2-phenyl-1-[6-(1H-1,2,3,4-tetrazol-5-yl)pyridin-2-ylmethyl]-1H-indole

Rendimiento 82.2%

Disolventes

water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawhile heated to reflux
2. 2
   workup.WAITThe reaction mixture was left
3. 3
   workup.STIRRINGby stirring at room temperature for 30 minutes
4. 4
   OtroThe organic layer was separated
5. 5
   Extracciónthe aqueous layer was extracted with ethyl acetate
6. 6
   LavadoThe combined organic layer was washed with saturated brine
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol)

Procedimiento

To a mixture of 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile (95 mg), isopropyl alcohol (6 mL), and water (4 mL) were added sodium azide (36 mg) and zinc bromide (32 mg). This mixture was stirred overnight while heated to reflux. The reaction mixture was left to cool to room temperature, and then diluted with ethyl acetate. To the mixture was added 2 mol/L hydrochloric acid (4 mL), followed by stirring at room temperature for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined 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: dichloromethane-methanol) to obtain the title compound (88 mg). 1H-NMR (DMSO-d6) δ ppm: 3.78 (3H, s), 5.61 (2H, s), 6.54 (1H, d, J=7.8 Hz), 6.66 (1H, d, J=0.4 Hz), 6.78 (1H, dd, J=2.5, 8.9 Hz), 7.16 (1H, d, J=2.5 Hz), 7.29 (1H, d, J=8.9 Hz), 7.35-7.55 (5H, m), 7.90 (1H, t, J=7.8 Hz), 8.05 (1H, d, J=7.8 Hz). ESI-MS (m/z): 383 (M+H)+

Fuente