[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.Cl([O-])=[O:13].[Na+].O1CCOCC1.S(=O)(=O)(O)N>O>[F:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]([CH:3]=1)[C:10]([OH:13])=[O:11]In a round bottom flask, 5-fluoro-2-methoxy-pyridine-3-carbaldehyde (37, 0.500 g, 3.22 mmol) was combined with sodium chlorite (0.6734 g, 5.957 mmol), 30 mL of 1,4-dioxane, 10 mL of water, and sulfamic acid (2.39 g, 24.6 mmol). The reaction mixture was stirred at room temperature for 5 minutes, then poured into 100 mL of water and extracted with 100 mL of ethyl acetate. The organic layer was washed with water, brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (150, 512 mg), used in the next step without further purification.
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