反应详情

A resealable tube was charged with 6-hydroxy-1-naphthoic acid (0.035 g, 0.187 mmol), cesium carbonate (0.183 g, 0.561 mmol), and DMF (1.0 mL). The system was flushed with argon, the tube was sealed, and the mixture stirred at RT for 15 min. 4-Chloro-6,7-dimethoxyquinoline-3-carboxamide (0.050 g, 0.187 mmol) mL) was added (along with a 1 mL DMF rinse), and the system was again flushed with argon. The tube was sealed and the mixture stirred at 60° C. for 26 h. The reaction mixture was diluted with water (2.5 mL) and 6 N HCl (aq) was added dropwise with stirring until the pH of the solution was 5-6. The resulting precipitate was filtered and washed with water. The filter cake was dried under vacuum to afford 6-(3-carbamoyl-6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid as a tan solid. MS (ESI, pos. ion) m/z: 419.0 (M+H). Mass Calc'd for C23H18N2O6: 418.

1. customThe system was flushed with argon
2. customthe tube was sealed
3. washrinse), and the system
4. customwas again flushed with argon
5. customThe tube was sealed
6. stirringthe mixture stirred at 60° C. for 26 h
7. additionThe reaction mixture was diluted with water (2.5 mL) and 6 N HCl (aq)
8. additionwas added dropwise
9. stirringwith stirring until the pH of the solution
10. filtrationThe resulting precipitate was filtered
11. washwashed with water
12. customThe filter cake was dried under vacuum