Sodium Azide → 3-(Azidomethyl)-5-bromopyridine
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]OS(C)(=O)=O)[CH:5]=[N:6][CH:7]=1.[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C.O>[N:14]([CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[N+:15]=[N-:16]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of crude methanesulfonic acid 5-bromo-pyridin-3-ylmethyl ester (4.20 g) in DMF (60 mL) was added NaN3 (10.0 g, 153.8 mmol). The mixture was stirred under N2 overnight then diluted with water. The mixture was extracted with EtOAc (2×300 mL) and the combined organic layers washed with water before drying over Na2SO4. The solution was concentrated in vacuo to afford crude 3-azidomethyl-5-bromo-pyridine (2.04 g) as a dark brown oil. This crude material was used directly in the next step.