Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([CH3:16])([CH3:15])[O:9][SiH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1.C([Li])CCC.[F:22][C:23]1[CH:34]=[CH:33][C:26]([C:27](N(OC)C)=[O:28])=[CH:25][CH:24]=1>CCOCC>[C:11]([SiH2:10][O:9][C:8]([CH3:16])([CH3:15])[C:6]1[CH:7]=[C:2]([C:27]([C:26]2[CH:33]=[CH:34][C:23]([F:22])=[CH:24][CH:25]=2)=[O:28])[CH:3]=[N:4][CH:5]=1)([CH3:14])([CH3:13])[CH3:12]To a solution of 3-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridine (1G) (1.0 g, 3.3 mmol) in 15 mL of ether at −75° C., is added n-butyl lithium (1.4 mL, 3.6 mmol, 2.5M in hexane) drop wise. After being stirred at −75° C. for 30 minutes, a solution of 4-fluoro-N-methoxy-N-methyl-benzamide (0.69 g, 3.8 mmol) in 5 mL of ether is added to the reaction solution drop wise. After being stirred at −75° C. for 1 hour, the reaction solution is warmed to room temperature in 1 hour, and quenched by addition of 10 mL of water. The mixture is extracted with 2×15 mL of EtOAc. After concentration, the crude product is purified by chromatography (heptane 90%, EtOAc 10%) to give [5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-3-yl]-(4-fluoro-phenyl)-methanone (1H) (0.79 g, Yield 69%) as colorless liquid. MS (ESI) m/e 346 (M+H+).
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