Br[C:2]1[CH:3]=[C:4]([Cl:13])[C:5]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:21][OH:22].CN([CH:26]=[O:27])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O>[Cl:13][C:4]1[C:5]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[N:6][CH:7]=[C:2]([CH:3]=1)[C:21]([O:27][CH3:26])=[O:22]A mixture of 5-bromo-3-chloro-2-(cyclopropylmethoxy)pyridine (3.00 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (470 mg), triethylamine (3.19 mL), methanol (3 mL) and DMF (30 mL) was stirred at 80° C. for 15 hr under a carbon monoxide atmosphere. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was 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 (2.53 g).
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