[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1.OS(O)(=O)=O.[I:24](O)(=O)(=O)=O.II>C(O)(=O)C>[Cl:1][C:2]1[C:3]([I:24])=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1To a solution of 8-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (1 g, 3.87 mmol) prepared as described in Example 16, Part G, in acetic acid (30 mL) was added H2SO4 (0.021 mL, 0.387 mmol) and periodic acid (0.881 g, 3.87 mmol). The solution was heated at 80° C. for 20 min then iodine (0.294 g, 1.160 mmol) was added. The mixture was stirred for another 3 h at 80° C. The solution was cooled to room temperature then concentrated under reduced pressure. EtOAc was added to the residue and the layer was washed with saturated aqueous NaHCO3 then H2O. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford 8-chloro-9-iodo-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (1.2 g, 3.12 mmol, 81% crude yield) as an off-white solid. The material was carried on without further purification. LC/MS (ESI) m/e 385.0 [(M+H)+, calcd for C14H11ClIN2O, 385.0]; LC/MS retention time (method B): tR=1.09 min.
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