Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[CH:7][CH:6]=2.C([C:14](CC)([C:18]([O-:20])=[O:19])C([O-])=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].N1C=CC=[CH:31][C:30]=1C(O)=O>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[N:4]1[C:5]2[C:10](=[N:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([CH2:14][C:18]([O:20][CH2:30][CH3:31])=[O:19])[CH:3]=1A mixture of 3-bromo-1,5-naphthyridine (540 mg, 2.58 mmol), diethylmalonate (0.8 mL, 5.17 mmol) and cesium carbonate (2.53 g, 7.75 mmol) in 1,4-dioxane (6 mL) was degassed with argon for 15 min then picolinic acid (64 mg, 0.517 mmol) and CuI (50 mg, 0.258 mmol) was added. The mixture was heated in a sealed tube at 110° C. for 24 hours then cooled to room temperature, diluted with ethyl acetate (10 mL), washed with water (10 mL) and brine (10 mL). The organic phase was dried over sodium sulphate then evaporated in vacuo and purified by column chromatography on silica gel (hexane:EtOAc 70:30) to afford 450 mg of ethyl 1,5-naphthyridin-3-ylacetate.
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