[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:10](OC)=[O:11])=[N:6][C:7]=1[O:8][CH3:9].CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][OH:11])=[N:6][C:7]=1[O:8][CH3:9]To a solution of methyl 5-bromo-6-methoxypicolinate (249 mg, 1.01 mmol) in dichloromethane (10 mL) added DIBAL-H in CH2Cl2 (1M, 3.04 mL) at −78° C. The reaction was immediately warmed to room temperature then stirred at room temperature for 1 hr. LCMS indicated that the reaction was complete. To the reaction mixture was added saturated aqueous NaK tartrate. It was stirred for 30 min. The reaction mixture was extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as a white solid (205 mg, 93.3%).
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