[Br:1][C:2]1[C:3](Cl)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[N-:12]=[N+:13]=[N-:14].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[N:12]([C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]2[NH:8][CH:9]=[CH:10][C:4]=12)=[N+:13]=[N-:14]5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (1.5 g, 6.5 mmol), sodium azide (2.11 g, 32 mmol), and ammonium chloride (1.73 g, 32 mmol) were suspended in anhydrous dimethylformamide (10 mL). The reaction was heated to 110° C. for 19 h. The reaction mixture was diluted with water and the solids were collected. The solids were dissolved in a mixture of acetone and ethylacetate, the solution was filtered and concentrated to afford 4-Azido-5-bromo-1H-pyrrolo[2,3-b]pyridine (670 mg, 2.8 mmol, 43%). MS: m/z 238.0/240.0 (M+H+).
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