Br[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[C:20]([CH:28]=[CH:29][CH:30]=2)[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[OH:9][CH2:8][C:6]1[N:7]=[C:2]([C:18]2[CH:19]=[C:20]([CH:28]=[CH:29][CH:30]=2)[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:3]=[CH:4][CH:5]=1To a solution of (6-bromopyridin-2-yl)methanol (811 mg) in DME (20 mL) was added Pd(PPh3) 4 (453 mg) at ambient temperature under N2 gas atmosphere. After stirring for 20 minutes, ethyl [3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetate (1.20 g) and a solution of 2M Na2CO3 aqueous solution (5.88 mL) were added and the mixture was refluxed for 7 hours. The mixture was cooled to ambient temperature and partitioned between EtOAc (40 mL) and water. The organic layer was washed with saturated NaHCO3 aqueous solution, water and then brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=10:1) to give ethyl {3-[6-(hydroxymethyl)pyridin-2-yl]phenoxy}acetate (297 mg) as a colorless oil.
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