反应详情

温度

110 °C

N-(2-chloro-5-(3-oxo-4-phenyl-3,4-dihydroquinoxalin-6-yl)pyridin-2-yl)dimethylaminosulfonamide. To a 5 mL microwave tube was added N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)dimethylaminosulfonamide (0.079 g, 0.219 mmol), 7-bromo-1-phenylquinoxalin-2(1H)-one (0.060 g, 0.199 mmol), 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) (0.015 g, 0.020 mmol), sodium carbonate (0.249 mL, 0.498 mmol), and dioxane (3 mL). The resulting mixture was sealed and subject to microwave heating at 110° C. for 20 min. The reaction mixture 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 by column chromatography (12 g, 3% MeOH and 32% EtOAc in DCM) to afford the desired product as a light yellow solid (65.0 mg). MS (ESI pos. ion) m/z: calcd for C21H18ClN5O3S: 455.1; found: 455.8 [M+1]. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.80 (s, 6 H) 6.76-6.86 (m, 2 H) 7.35 (d, J=7.16 Hz, 2 H) 7.53 (d, J=8.33 Hz, 1 H) 7.58-7.72 (m, 3 H) 7.94 (s, 1 H) 8.04 (d, J=8.18 Hz, 1 H) 8.20 (s, 1 H) 8.45 (s, 1 H).

1. customThe resulting mixture was sealed
2. customThe reaction mixture was partitioned between pH 7 buffer (1M Tris-HCl) and DCM
3. extractionThe aqueous layer was extracted with DCM (2×10 mL)
4. dry with materialThe combined organic layers were dried over MgSO4
5. concentrationconcentrated
6. customThe crude product was purified by column chromatography (12 g, 3% MeOH and 32% EtOAc in DCM)