[Br:1][C:2]1[C:3]([NH2:11])=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:7]=1.Cl[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][O-].[K+].S(=O)(=O)(O)O.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[C:3]2[N:4]([C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:11]=2)[CH:5]=[C:6]([CH:8]2[CH2:9][CH2:10]2)[CH:7]=1A mixture of 3-bromo-5-cyclopropylpyridin-2-amine (0.753 g), potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (1.30 g), sulfuric acid (0.208 mL) and ethanol (15 mL) was heated with reflux overnight. The reaction mixture was neutralized with 1N sodium hydroxide at 0° C., and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (565 mg).
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