3-Aminophenol → 6-bromo-2-(3-hydroxyphenyl)amino-N-(5-methyl-3-phenylisoxazol-4-yl)-4-quinolinecarboxamide

Participants

Reaction Steps

The solution of 6-bromo-2-chloro-N-(5-methyl-3-phenylisoxazol-4-yl)-4-quinolinecarboxamide (50 mg) and 3-aminophenol (50 mg) in ethanol (2 mL) and triethylamine (0.1 mL) was microwaved at 170° C. for one hour. The reaction mixture was then diluted with ethyl acetate (60 mL). The organic solution was washed with water (60 mL), 1N HCl aqueous solution (2×60 mL), separated, dried, evaporated and re-crystallized from ethyl acetate and hexanes to give 6-bromo-2-(3-hydroxyphenyl)amino-N-(5-methyl-3-phenylisoxazol-4-yl)-4-quinolinecarboxamide (50 mg) as a yellow solid. 1H NMR (acetone-d6): δ 2.53 (s, 3H), 6.72 (d, J=6.9 Hz, 1H), 7.15 (d, J=7.8 Hz, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.51 (m, 4H), 7.60 (s, 1H), 7.78 (m, 3H), 7.87 (d, J=9.0 Hz, 1H), 8.15 (d, J=2.1 Hz, 1H), 8.70 (br, 1H), 9.77 (br, 1H); LCMS: ret. time: 25.49 min.; purity: 1100%; MS (m/e): 514.91 (M+).

Provenance & Evidence