反应详情

温度

100 °C

1-butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate (1.00 g, 2.39 mmol), potassium phosphate tribasic (1.52 g, 7.17 mmol), palladium(II) acetate (0.0540 g, 0.239 mmol), and tricyclohexylphosphine (0.134 g, 0.478 mmol) were combined in pressure vessel. Toluene (20 ml), water (6.67 ml), and isopropenylboronic acid pinacol ester (0.899 ml, 4.78 mmol) were added. The resulting suspension was purged with argon (subsurface bubbling) for 10 min. The reaction mixture was stirred in a sealed pressure vessel at 100° C. for 2.5 h. After cooling the reaction mixture was diluted with EtOAc, and washed with aqueous ammonium chloride. The organic layer was dried over sodium sulfate, filtered, and concentrated to a crude residue that was adsorbed on to silica gel and purified by column chromatography on silica gel eluting with an EtOAc/hexane gradient to afford 1-butoxy-9-fluoro-6-isopropenylbenzo[c]-1,6-naphthyridine. LRMS (ESI) calc'd for (C19H19FN2O) [M+H]+, 311.1; found 311.1.

1. customThe resulting suspension was purged with argon (subsurface bubbling) for 10 min
2. temperatureAfter cooling the reaction mixture
3. additionwas diluted with EtOAc
4. washwashed with aqueous ammonium chloride
5. dry with materialThe organic layer was dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated to a crude residue that
8. custompurified by column chromatography on silica gel eluting with an EtOAc/hexane gradient