[I:1]I.[CH2:3]([NH:5][C:6](=[O:24])[C:7]1[CH:12]=[C:11]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][NH:19]3)=[CH:15][CH:14]=2)[C:10]([CH3:22])=[C:9]([F:23])[CH:8]=1)[CH3:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.[OH-].[Na+].O>[CH2:3]([NH:5][C:6](=[O:24])[C:7]1[CH:12]=[C:11]([C:13]2[CH:21]=[C:20]3[C:16]([C:17]([I:1])=[N:18][NH:19]3)=[CH:15][CH:14]=2)[C:10]([CH3:22])=[C:9]([F:23])[CH:8]=1)[CH3:4]Iodine (0.153 g) was added to a stirred solution of N-ethyl-3-fluoro-5-(1H-indazol-6-yl)-4-methylbenzamide (Intermediate 18, 0.15 g) in 1,4-dioxan (4 ml) and aqueous sodium hydroxide (2M, 4 ml) then stirred at room temperature for 45 min. The reaction mixture was treated aqueous citric acid (20%, 20 ml) followed by sodium metabisulphite (2 g). The mixture was diluted with water then extracted with ethyl acetate (2×30 ml). The organic extracts were washed with water (30 ml) dried (Na2SO4) and concentrated under vacuum to give the title-compound as a pale yellow foam (0.21 g).
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