반응 #2487465

반응 방정식

hydrochloric acid

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

isopropyl alcohol

sodium azide

→

title compound

수율 82.2%

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

수율 82.2%

용매

water

ethyl acetate

반응 조건

후처리

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

실험 절차

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)+

출처