Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.C([Li])CCC.[CH3:15][C:16]([CH3:18])=[O:17]>C1(C)C=CC=CC=1>[Br:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([C:16]([OH:17])([CH3:18])[CH3:15])=[N:3][CH:4]=1To 2,5-dibromo-3-fluoropyridine in toluene at −78° C. was added n-butyllithium drop wise. The resulting solution was stirred at −78° C. for 1.5 hours. Then at −78° C., added acetone drop wise to the reaction mixture and continue to stir reaction at −78° C. for 2 hours at which point LC-MS and TLC indicated the reaction was complete. The reaction was warmed to 0° C. and quenched with saturated ammonium chloride solution (aq.) and then diluted with water (50 mL) and extracted with ethyl acetate (2×100 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to afford crude product. Gradient column chromatography on silica eluting with 0 to 30% EtOAc/hexanes gave the desired product (1.04 g).
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