Iodine → HCID 178477913, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[N:9][NH:10][C:5]2=[CH:4][CH:3]=1.[OH-].[K+].[I:13]I>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([I:13])=[N:9][NH:10][C:5]2=[CH:4][CH:3]=1Participants
7
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[N:9][NH:10][C:5]2=[CH:4][CH:3]=1.[OH-].[K+].[I:13]I>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([I:13])=[N:9][NH:10][C:5]2=[CH:4][CH:3]=1
To a solution of 5-chloro-1H-pyrazolo[4,3-b]pyridine (100 mg, 0.65 mmol) in DMF (5 mL), was added KOH (91 mg, 1.63 mmol), I2 (247 mg, 0.98 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 5 min and then stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and water. The organic phase was washed by sat. NaHSO3, dried over MgSO4, filtered, concentrated, and purified by silica gel column, eluting by 0-70% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C6H3ClIN3: 279.9 (M+H+); Found: 279.3 (M+H+).
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