反应 #2487465

反应方程式

hydrochloric acid

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

isopropyl alcohol

sodium azide

→

title compound

收率 82.2%

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

收率 82.2%

溶剂

water

ethyl acetate

反应条件

后处理

1. 1
   温度while heated to reflux
2. 2
   workup.WAITThe reaction mixture was left
3. 3
   workup.STIRRINGby stirring at room temperature for 30 minutes
4. 4
   其他The organic layer was separated
5. 5
   萃取the aqueous layer was extracted with ethyl acetate
6. 6
   洗涤The combined organic layer was washed with saturated brine
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   浓缩concentrated under reduced pressure
9. 9
   其他The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol)

实验过程

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)+

来源