Reaktion #607707

Reaktionsgleichung

trimethylsilyl azide

dibutyl(oxo)stannane

trimethylsilyl azide

6-Bromo-1-methyl-1H-indazole-4-carbonitrile

sodium hydroxide

→

title compound

Ausbeute 99.4%

6-Bromo-1-methyl-4-(1H-tetrazol-5-yl)-1H-indazole

Ausbeute 99.4%

Lösungsmittel

toluene

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture continued stirring at 110° C. under nitrogen for 44 h
2. 2
   SonstigeThe solvent was removed in vacuo
3. 3
   Sonstigeto give a white solid
4. 4
   Temperaturthe mixture heated to 50° C.
5. 5
   Filtrationfiltered whilst hot
6. 6
   Sonstigeto remove insoluble impurities
7. 7
   TemperaturThe filtrate was cooled
8. 8
   workup.ADDITIONacidified via dropwise addition of 2M hydrochloric acid
9. 9
   FiltrationThe resultant precipitate was filtered
10. 10
    Sonstigedried in a vacuum oven

Vorschrift

6-Bromo-1-methyl-1H-indazole-4-carbonitrile (514 mg, 2.177 mmol) was dissolved in toluene (20 mL) and dibutyl(oxo)stannane (108 mg, 0.435 mmol) and trimethylsilyl azide (0.573 mL, 4.35 mmol) were added over 2 mins. The mixture was then stirred at 110° C. under nitrogen for 28 h. Further trimethylsilyl azide (0.03 mL, 0.228 mmol) was added and the mixture continued stirring at 110° C. under nitrogen for 44 h. The solvent was removed in vacuo to give a white solid. 2M sodium hydroxide in methanol was added and the mixture heated to 50° C. and then filtered whilst hot to remove insoluble impurities. The filtrate was cooled and then acidified via dropwise addition of 2M hydrochloric acid. The resultant precipitate was filtered and dried in a vacuum oven to give the title compound as a white solid (604 mg).

Quelle