[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[Br:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH2:19]Cl)[CH:14]=1.[NH4+].[Cl-]>C1COCC1.C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[CH:2]([CH2:19][C:15]1[CH:14]=[C:13]([Br:12])[CH:18]=[CH:17][N:16]=1)[C:1]([O:8][CH3:9])=[O:7]To a solution of dimethyl malonate (3.83 g) in dry THF (10 mL) at 0° C. was added NaH (463 mg) and the reaction mixture was stirred at rt for 30 min. A solution of 4-bromo-2-chloromethyl-pyridine (1.99 g) in dry THF (10 mL) was added and the reaction mixture stirred at rt for 15 h. It was then diluted with DCM, treated with a sat. aq. NH4Cl solution and the org. layers were washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The title compound was obtained, after purification by CC (Hept/EA 100:0 to 50:50), as a yellow oil (1.65 g; 57% yield).
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