[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9](O)=[O:10])[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].B(F)(F)F.CCOCC>O1CCCC1.[Cl-].[Na+].O.[Cl-].[NH4+].C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=1A solution of (6-bromopyridin-2-yl)acetic acid (1.1 g, 5.09 mmol) in tetrahydrofuran (20 ml) was cooled to 0° C. Sodium borohydride (0.385 g, 10.18 mmol) was slowly added followed by the addition of boron trifluoride diethyl etherate (1.29 ml, 10.18 mmol). The reaction was allowed to come to room temperature. After 2 hrs, the reaction was diluted with brine, ammonium chloride and ethyl acetate. After layer separation, the organic layer was dried over sodium sulfate, filtered and concentrated. The crude residue was purification by silica gel chromatography (3:7 hexane:ethyl acetate) to yield the title compound.
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