反应详情

A suspension of 4.80 g (21.60 mmol) 8-bromo-2-methylquinoline (commercially available from ACB Block Ltd, Moscow, Russia), 0.89 g (1.10 mmol) PdCl2dppfCH2Cl2, 4.48 g (32.40 mmol) potassium vinyl tetrafluoroborate and 3.10 ml (22.10 mmol) triethylamine in 150 ml ethanol was heated at reflux for 3 h. The resulting yellow suspension was filtered and the filtrate evaporated to dryness. The residue was suspended in ethyl acetate, filtered and the filtrate extracted with water. The organic layer was evaporated to dryness and the isolated crude product purified by silica gel chromatography (CH2Cl2/ethyl acetate 98:2) to yield 2.68 g (73%) of the title compound as a colorless oil. MS: 169.1 (M+). 1H-NMR (300 MHz, CDCl3): 2.74 (s, 1H); 5.47 (dd, J=11.1, 1.6 Hz, 1H); 5.97 (dd, 17.9, 1.6 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H); 7.43 (t, J=7.7 Hz, 1H); 7.66 (dd, J=8.1, 1.2 Hz, 1H); 7.87 (dd, J=7.3, 1.2 Hz, 1H); 7.97 (d, J=8.4 Hz, 1H); 8.05 (dd, J=17.9, 11.1 Hz, 1H).

1. temperaturewas heated
2. temperatureat reflux for 3 h
3. filtrationThe resulting yellow suspension was filtered
4. customthe filtrate evaporated to dryness
5. filtrationfiltered
6. extractionthe filtrate extracted with water
7. customThe organic layer was evaporated to dryness
8. customthe isolated crude product
9. custompurified by silica gel chromatography (CH2Cl2/ethyl acetate 98:2)