2,8-Dichloro-quinoline-3-carbaldehyde → 8-Chloro-2-(6-methoxypyrazin-2-yl)quinoline-3-carbaldehyde
反応式
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([Sn](CCCC)(CCCC)CCCC)[N:18]=1>O1CCOCC1>[Cl:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:19]1[CH:20]=[N:21][CH:22]=[C:17]([O:16][CH3:15])[N:18]=1)[C:11]([CH:12]=[O:13])=[CH:10]2参加物
4
反応条件
- 温度
- 110 °C
実験手順
A mixture of 2,8-dichloroquinoline-3-carbaldehyde (0.5 g, 2.21 mmol), 2-methoxy-6-(tributylstannanyl)pyrazine (1.0 g, 2.51 mmol) and tetrakis(triphenyl-phosphine)palladium(0) (0.2 g, 0.173 mmol) in 1,4-dioxane (10 mL) was degassed and heated at 110° C. overnight. The mixture was allowed to cool to room temperature and diluted with EtOAc. The resulting solid was collected by filtration, washed with EtOAc, then ether, and dried to give the title compound (0.42 g, 63%) as a yellow solid. δH(DMSO-d6) 10.58 (s, 1H), 9.24 (s, 1H), 8.93 (s, 1H), 8.53 (s, 1H), 8.27 (dd, J 8.3, 1.2 Hz, 1H), 8.17 (dd, J 7.5, 1.2 Hz, 1H), 7.75 (m, 1H), 3.96 (s, 3H). LCMS (ES+) 300 (M+H)+, RT 1.51 minutes.