[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([CH2:13]O)[N:10]=[CH:9]2)=[N:6][CH:7]=1.O=S(Cl)Cl.[N-:19]=[N+:20]=[N-:21].[Na+].O>CC#N.CCOC(C)=O>[N:19]([CH2:13][C:11]1[N:10]=[CH:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH:12]=1)=[N+:20]=[N-:21]To a suspension of (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanol (520 mg, 2.05 mmol) in CH3CN (5 mL) at room temperature was added SOCl2 (2.5 mL). With the addition, the suspension became clear. After 10 min of stirring, the mixture was concentrated in vacuo. The residue was dissolved in DMF (12 mL), and NaN3 (565 mg, 8.69 mmol) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 2-(4-(azidomethyl)-1H-imidazol-1-yl)-5-bromopyridine (500 mg).
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