反应详情

温度

100 °C

To a solution of cinnolin-4(1H)-one in DMF (0.1 M) was added K2CO3 (1.2 eq) and methyl 5-(bromomethyl)-2-fluorobenzoate (prepared as described in US 2007/0021427 A1, 1 eq). The mixture was stirred and heated to 100° C. for 1 h. After cooling to RT the solvent was removed under reduced pressure and the residue was partitioned between DCM and H2O. The organic phase was washed with brine, dried (Na2SO4) and filtered and the solvent was removed under reduced pressure. The product was isolated by flash chromatography on silicagel, using a gradient of DCM/MeOH (from 0% to 10% MeOH in 10 CV). The 2-[4-fluoro-3-(methoxycarbonyl)benzyl]cinnolin-2-ium-4-olate was eluted after the title compound.

1. temperatureAfter cooling to RT the solvent
2. customwas removed under reduced pressure
3. customthe residue was partitioned between DCM and H2O
4. washThe organic phase was washed with brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customthe solvent was removed under reduced pressure
8. customThe product was isolated by flash chromatography on silicagel
9. washThe 2-[4-fluoro-3-(methoxycarbonyl)benzyl]cinnolin-2-ium-4-olate was eluted after the title compound