[I:1][C:2]1[C:3](=[O:21])[C:4]2[C:9]([O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:8]1[NH:18][N:19]=[CH:20][C:7]1=[CH:6][CH:5]=2.[Cl:22][O-].[Na+]>CCO>[Cl:22][C:20]1[C:7]2=[CH:6][CH:5]=[C:4]3[C:9]([O:10][C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[C:2]([I:1])[C:3]3=[O:21])=[C:8]2[NH:18][N:19]=1To a stirred solution of 7-iodo-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one (73 mg, 0.188 mmol) in EtOH (10 mL), with cooling in a 10° C. water bath, was added sodium hypochlorite (10% aqueous solution, 9 mL). After 15 minutes, the temperature was allowed to increase to RT. After a further 30 minutes, the reaction mixture was concentrated in vacuo and the remaining reside was partitioned between EtOAc and water. The resulting biphasic mixture was separated, the aqueous phase was further extracted with EtOAc, the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and evaporated in vacuo to afford the title compound (44 mg, 55%) as a cream solid. LCMS (Method H): RT=3.75 min, [M+H]+=423/425.
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