反应详情

温度

100 °C

To a 5 mL microwave tube was added N-(5-(6-bromoimidazo[1,2-a]pyridin-3-yl)-2-chloropyridin-3-yl)dimethylaminosulfonamide (0.080 g, 0.186 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine (0.061 g, 0.223 mmol), 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) (0.014 g, 0.019 mmol), sodium carbonate (0.232 mL, 0.464 mmol), and dioxane (2 mL). The resulting mixture was sealed and underwent microwave heating at 100° C. for 20 min. The solvent was removed. The residue was partitioned between pH 7-buffer (1M TRIS-HCL) and DCM. The aqueous layer was extracted with DCM (2×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, 40 g SiO2, DCM:MeOH (2M NH3)=90%:10% Flow=40 mL/min) to afford the desired product as light yellow solid (25.0 mg). MS (ESI pos. ion) m/z: 496.8. Calcd exact mass for C20H16ClF3N6O2S: 496.1. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.92 (s, 6H) 6.93 (br. s., 1H) 7.78 (d, J=4.82 Hz, 1H) 7.91 (d, J=8.77 Hz, 1H) 7.96 (s, 1H) 8.07 (s, 1H) 8.22 (s, 1H) 8.33-8.44 (m, 2H) 8.70 (s, 1H) 8.90 (d, J=5.26 Hz, 1H).

1. customThe resulting mixture was sealed
2. customThe solvent was removed
3. customThe residue was partitioned between pH 7-buffer (1M TRIS-HCL) and DCM
4. extractionThe aqueous layer was extracted with DCM (2×10 mL)
5. dry with materialThe combined organic layers were dried over MgSO4
6. concentrationconcentrated
7. customThe crude product was purified