[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(OCC)(=O)C.O>CN(C)C=O.C(N(CC)CC)C>[Cl:1][C:2]1[N:11]=[C:10]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]To a solution of 1.5 g of methyl 2,6-dichloro-5-fluoronicotinate in 15 mL of N,N-dimethylformamide, 0.93 mL of triethylamine was added at room temperature, and thereto was dropped 0.56 mL of pyrrolidine. The mixture was stirred at the same temperature for 1 hour, 56 μL of pyrrolidine was further added, and the mixture was stirred for 50 minutes. After leaving overnight, ethyl acetate and water were added to the reaction mixture. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.7 g of methyl 2-chloro-5-fluoro-6-(pyrrolidin-1-yl)nicotinate as a white solid.
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