O[O:2][S:3]([O-:5])=O.[K+].[C:7](#N)C.[Cl:10][C:11]1[CH:12]=[C:13]2[NH:20][C:19](SC)=[N:18][C:14]2=[N:15][C:16]=1[I:17]>O>[Cl:10][C:11]1[CH:12]=[C:13]2[NH:20][C:19]([S:3]([CH3:7])(=[O:5])=[O:2])=[N:18][C:14]2=[N:15][C:16]=1[I:17]Oxone (20.8 g, 33.8 mmol) was added to an acetonitrile (100 mL)/water (100 mL) suspension of 6-chloro-5-iodo-2-(methysulfanyl)-1H-imidazo[4,5-b]pyridine (5.0 g, 15.4 mmol) and the reaction was allowed to stir for 18 h at rt. The suspension was filtered through a sintered glass funnel and the filtrate was partitioned between ethyl acetate and saturated sodium bisulfate. The ethyl acetate layer was washed with brine, dried over magnesium sulfate and concentrated to afford the title compound as a white solid that was used in subsequent steps without further purification. Solubility precludes purification and this was used as is. LC-MS: calculated for C7H5ClN3O2S 357.56, observed m/e: 357.07 (M+H)+ (Rt 1.36/4 min) 1H NMR δ (ppm) (DMSO-d6): 8.44 (1H, s), 3.53 (3H, s).
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