[ CAS No. 55808-09-8 ] {[proInfo.proName]}

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• [ 55808-09-8 ]
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• [ 286371-44-6 ]
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• [ 475108-18-0 ]

Yield	Reaction Conditions	Operation in experiment
12.9 g	With pyridine In N,N-dimethyl acetamide at 80℃; for 5 h;	A solution of 5-methylisoxazol-3-amine (5.3 g, 0.054 mol) and pyridine (17.2 g, 0.22 mol) in dimethylacetamide (30 mL) was stirred and cooled in an ice-water bath. Methyl chloroformate (5.1 g,0.054 mol) was added slowly and keeping the reaction temperature below 10°C. The reaction mixturewas stirred at the ambient temperature for another 2 h to give the methyl (5-methylisoxazol-3-yl)carbamate (14). Then 2-cholo-4-((6,7-dimethoxyquinolin-4-yl)oxy)-aniline 9 (12.0 g, 0.036 mol) was added and the reaction mixture was stirred at 80° C for 5 h. The reaction suspension was cooled to room temperature and added into water (300 mL) and MeOH (100 mL) and stirred for 30 min. The resulting solid was filtered, washed with water (50 mL × 2), and dried at 50°C to give the crude product 1, which was takenup in EtOAc : EtOH = 1:1 (v:v) (60 mL) and heated to reflux for 30 min, then cooled to room temperature for 1 h, the resulting solid was filtered off and washed with EtOAc (20 mL × 2), dried at 50°C for 3 h to afford 1 (12.9 g, 79percent) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 2.35 (s, 3H), 3.93 (s, 3H),3.95 (s, 3H), 6.52 (d, J = 5.2 Hz, 1H), 6.57 (d, J = 8.8 Hz, 1H), 7.28 (dd, J = 2.4, 8.8 Hz, 1H), 7.42 (s, 1H),7.49 (s, 1H), 7.51 (d, J = 2.4 Hz, 1H), 8.21 (d, J = 8.8 Hz, 1H), 8.51 (d, J = 5.2 Hz, 1H), 9.02 (s, 1H),10.42 (s, 1H). ESI-MS (m/z) 455.1 [M+H]+.HPLC: tR: 5.446 min, purity: 98.9percent.