[H-].[Li+].[O:3]=[C:4]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=C[CH:7]=[CH:6][NH:5]1.Br[CH2:15][CH:16]1[CH2:18][CH2:17]1.C[N:20](C=O)C>CCOC(C)=O>[CH:18]1([CH2:17][N:5]2[CH:6]=[CH:7][N:20]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]2=[O:3])[CH2:16][CH2:15]1LiH (7.7 mg, 0.97 mmol) was added to the solution of methyl 2-oxo-1,2-dihydropyridine-3-carboxylate (0.10 g, 0.65 mmol) in DMF (3 mL) at 0° C. After stirring for 30 minutes, (bromomethyl) cyclopropane (0.18 g, 1.30 mmol) was added to the reaction mixture at the temperature, and the reaction was warmed to 50° C. After stirring for 3 days at 50° C., the reaction mixture was diluted with EtOAc, quenched with ice water, extracted with EtOAc, dried over MgSO4, and concentrated. The crude was purified by silica gel flash column chromatography (2% MeOH in CH2Cl2) to afford 87 mg (64%) of the desired product.
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