[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:29][OH:30].C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[N:29]\[OH:30])=[CH:4][CH:3]=1To a solution of 5-(3-(4-bromophenyl)-3-(2,4-difluorophenyl)propanoyl)-1-methyl-pyridin-2(1H)-one (0.2 g, 463 μmol) in ethanol (5 mL) and water (0.2 mL) was added hydroxylamine hydrochloride (80.4 mg, 1.16 mmol) and sodium hydrogencarbonate (77.7 mg, 925 μmol) and the resulting colourless suspension was heated at reflux (100° C. oil bath temperature) for 4.5 hours. After cooling down the reaction mixture was poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100). Colourless foam (0.205 g, 99%). MS (ESI+): m/z=449.1 ([M+H]+).
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