[Si]([O:18][C:19]1[CH:20]=[C:21]([F:26])[C:22](Cl)=[N:23][CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C.[CH2:34]([OH:36])[CH3:35].CN([CH:40]=[O:41])C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[F:26][C:21]1[C:22]([C:40]([O:36][CH2:34][CH3:35])=[O:41])=[N:23][CH:24]=[C:19]([OH:18])[CH:20]=1A mixture of 5-((tert-butyl(diphenyl)silyl)oxy)-2-chloro-3-fluoropyridine (29.5 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (5.59 g), triethylamine (10.7 mL), ethanol (300 mL) and DMF (300 mL) was stirred overnight at 80° C. under a carbon monoxide atmosphere. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (30.8 g) as a mixture with DMF.
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