1) Ammonia (200 mL, 5.2 mol) was added to a 500 mL three-necked flask, and compound IV (10 g, 39.8 mmol) obtained in step 3.3) was added to obtain mixture H;
2) The mixture H obtained in step 4.1) was placed at 60° C. After 4 hours of reaction, the mixture was cooled to room temperature to obtain mixture I; 4.3) Dichloromethane was added to mixture I, and extracted 3 times to obtain pale yellow compound V (yield 85.17%)
Methyl 4-chloro-7-methoxy-quinoline-6-carboxylate (120 mg) was dissolved in methanol (6 ml), 28% aqueous ammonia (6 ml) was added, and the mixture was stirred at 40°C overnight. The solvent was distilled off under reduced pressure, and the residue was purified by methanol-chloroform thin-layer chromatography to obtain 4-chloro-7-methoxy-quinoline-6-carboxamide (91 mg, yield 80%). 4-Chloro-7 -Methoxy-quinoline-6-carboxylic acid amide (91 mg), 5,6-dimethyl-[2,2′]bipyridin-3-ol (115 mg) and 4-dimethylaminopyridine (141 mg) was dissolved in dimethyl sulfoxide (3 ml), cesium carbonate (375 mg) was added to the solution, and the mixture was stirred at 130° C. overnight. The mixture was cooled to room temperature and water was added to the reaction mixture. The organic layer was extracted with chloroform, and the chloroform layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by thin-layer chromatography with a methanol-chloroform system to obtain the title compound (33 mg, yield 22%). 1H-NMR (CDCl3, 400 MHz): δ 2.40 (s, 3H), 2.67 (s, 3H), 4.13 (s, 3H), 5.92 (m, 1H), 6.39 (d, J = 5.4 Hz, 1H) , 7.08 (ddd, J = 1.2, 4.9, 7.6 Hz, 1H), 7.36 (s, 1H), 7.56 – 7.63 (m, 2H), 7.76 (m, 1H), 7.90 (m, 1H), 8.40 (m , 1H), 8.54 (d, J = 5.6 Hz, 1H), 9.27 (d, J = 1.0 Hz, 1H) Mass spectrum (ESI-MS, m/z): 423 (M+Na)+.