반응 #67109

반응 방정식

trimethylsilyl azide

dibutyl(oxo)stannane

trimethylsilyl azide

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

sodium hydroxide

→

title compound

수율 99.4%

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

수율 99.4%

용매

toluene

methanol

반응 조건

후처리

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

실험 절차

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).

출처