Reaktion #1555180

Reaktionsgleichung

1H-indol-5-amine

sodium azide

triethoxy ethane

→

5-(1H-tetrazol-1-yl)-1H-indole

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas brought to room temperature
2. 2
   workup.STIRRINGstirred for 10-12 h
3. 3
   SonstigeThe reaction was quenched with saturated NaHCO3
4. 4
   Extraktionthe mixture was extracted with ethyl acetate
5. 5
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed with brine
7. 7
   Trocknendried over anhydrous NaSO4
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeResultant residue was purified by flash column chromatography

Vorschrift

To a stirring solution of 1H-indol-5-amine (0.6 g, 4.52 mmol) in acetic acid (9 mL), sodium azide (0.42 g, 6.2 mmol) and triethoxy ethane (1.0 mL, 6.2 mmol) were added and stirred at 100° C. for 3 h. The reaction was brought to room temperature and stirred for 10-12 h. The reaction was quenched with saturated NaHCO3 and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous NaSO4 and concentrated in vacuo. Resultant residue was purified by flash column chromatography to yield 5-(1H-tetrazol-1-yl)-1H-indole. (0.174 g, 21%); MS: 186 (M+1).

Quelle