تفاعل #67109

معادلة التفاعل

trimethylsilyl azide

dibutyl(oxo)stannane

trimethylsilyl azide

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

sodium hydroxide

→

title compound

المردود 99.4%

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

المردود 99.4%

المذيبات

toluene

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture continued stirring at 110° C. under nitrogen for 44 h
2. 2
   أخرىThe solvent was removed in vacuo
3. 3
   أخرىto give a white solid
4. 4
   درجة الحرارةthe mixture heated to 50° C.
5. 5
   ترشيحfiltered whilst hot
6. 6
   أخرىto remove insoluble impurities
7. 7
   درجة الحرارةThe filtrate was cooled
8. 8
   workup.ADDITIONacidified via dropwise addition of 2M hydrochloric acid
9. 9
   ترشيحThe resultant precipitate was filtered
10. 10
    أخرىdried in a vacuum oven

الإجراء التجريبي

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).

المصدر