Reaktion #2043710

Reaktionsgleichung

aluminum azide

benzyl-{2-[2-(3,5-dimethylphenyl)-5-isocyanato-1H-indol-3-yl]ethyl } -(4-pyridin-3-yl-butyl)amine

→

title compound

Ausbeute 44.7%

1-[3{-2-[benzyl-(4-pyridin-3-yl-butyl)-amino]ethyl}-2-(3.5-dimethylphenyl)-1H-indol-5-yl]-1,4-dihydrotetrazol-5-one

Ausbeute 44.7%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturto reflux on an oil bath
3. 3
   Einengenconcentrated
4. 4
   workup.ADDITIONpoured into a mixture of 1M sodium potassium tartarate and ice
5. 5
   Sonstigethen partitioned between ethyl acetate and water
6. 6
   WaschenThe organic portion was washed successively with 1M sodium potassium tartarate, water and brine
7. 7
   Trocknenthen dried over sodium sulfate
8. 8
   SonstigePurification of the
9. 9
   Einengenconcentrate by flash chromatography on silica gel (methylene chloride:methanol, 88:12)

Vorschrift

To a solution of freshly prepared aluminum azide (0.6 mmol in 6 niL dry tetrahydrofuran) was added 120 mg benzyl-{2-[2-(3,5-dimethylphenyl)-5-isocyanato-1H-indol-3-yl]ethyl } -(4-pyridin-3-yl-butyl)amine and the mixture heated to reflux on an oil bath. After 20 hours, the mixture was cooled to room temperature concentrated poured into a mixture of 1M sodium potassium tartarate and ice, stirred vigorously for 40 minutes then partitioned between ethyl acetate and water. The organic portion was washed successively with 1M sodium potassium tartarate, water and brine then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 88:12) gave the title compound (58 mg).

Quelle