反应详情

温度

100 °C

To a solution of compound 5.2 ethyl 6-chloro-4-(4-(4-propionylpiperazin-1-yl)-3-(trifluoromethyl)phenylamino)quinoline-3-carboxylate (1 g, 1.6 mmol, 1 equiv.) in dioxane (5 mL) at room temperature was sequentially added 3-qunionline boronic acid 5.3 (350 mg, 2 mmol, 1.1 equiv.), PdCl2(Ph3P)2 (130 mg, 0.19 mmol, 0.1 equiv.), t-Bu-Xphos (78 mg, 0.19 mmol, 0.1 equiv.) and Na2CO3 (1N, 5.5 mL, 5.5 mmol, 3 equiv.). The mixture was degassed, sealed under argon, and heated overnight at 100° C. Upon cooling to room temperature, the mixture was diluted with EtOAc (20 mL), filtered through celite, and washed with EtOAc (20 mL×2). The resulting solution was concentrated and the residue was purified via flash chromagraphy (CH2Cl2: MeOH=30:1) to afford the desired product 5.4 ethyl 4′-(4-(4-propionylpiperazin-1-yl)-3-(trifluoromethyl)phenylamino)-3,6′-biquinoline-3′-carboxylate (360 mg; 31%). LC-MS: (M+H): 535.20

1. customThe mixture was degassed
2. customsealed under argon
3. temperatureUpon cooling to room temperature
4. additionthe mixture was diluted with EtOAc (20 mL)
5. filtrationfiltered through celite
6. washwashed with EtOAc (20 mL×2)
7. concentrationThe resulting solution was concentrated
8. customthe residue was purified via flash chromagraphy (CH2Cl2: MeOH=30:1)