Reaction #2487465

Reaction equation

hydrochloric acid

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

isopropyl alcohol

sodium azide

→

title compound

Yield 82.2%

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

Yield 82.2%

Solvents

water

ethyl acetate

Conditions

Workup

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

Procedure

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)+

Source