反应详情

A mixture of 1-ethyl-6-methoxy-1H-indole-3-carbonitrile (1.00 g, 5.00 mmol) in toluene (30 mL) was treated with triethylamine hydrochloride (1.03 g, 7.50 mmol) and sodium azide (0.49 g, 7.50 mmol) and was heated at reflux for 16 h. After cooling to room temperature, the reaction mixture was diluted with saturated NaHCO3 and extracted with EtOAc. The organic layer was then washed with additional NaHCO3 (2×). The combined aqueous phases were acidified to pH 2 with 6N HCl. The resultant thick precipitate was extracted with hot EtOAc (3×) and the combined organic phases were washed with saturated NaCl and dried and concentrated to give 0.55 g (45%) of 1-ethyl-6-methoxy-3-(1H-tetrazol-5-yl)-1H-indole as a yellow solid.

1. temperaturewas heated
2. temperatureat reflux for 16 h
3. extractionextracted with EtOAc
4. washThe organic layer was then washed with additional NaHCO3 (2×)
5. extractionThe resultant thick precipitate was extracted with hot EtOAc (3×)
6. washthe combined organic phases were washed with saturated NaCl
7. customdried
8. concentrationconcentrated