反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 90 °C
PROCEDURE
实验过程
(Some starting materials may be obtained from AstaTech, Inc. Princeton, N.J.) A 15 mL sealed pressure tube was charged with N-(5-bromo-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamide (120 mg, 0.318 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (90 mg, 0.350 mmol) in ethanol (1.5 mL). To this was added 5 mol % of Pd(PPh3)4 (18 mg, 0.016 mmol) and Na2CO3 (2M, 0.4 mL). The flask was flushed with argon, sealed and stirred at 90° C. for 4 hours. The crude mixture was partitioned between water and ethyl acetate, extracted with ethyl acetate (3×), dried over Na2SO4 and concentrated in vacuo. The Solids were taken up in minimal methylene chloride and purified via ISCO, 40 g RediSep® (Teledyne ISCO, Lincoln, Nebr.) column with a 20-100% gradient of ethyl acetate in hexanes, to afford the desired material. MS (ESI pos. ion) m/z calc'd for C21H16ClN3O3S: 425.1; found 426.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.83 (s, 3 H) 7.12 (d, J=8.80 Hz, 2 H) 7.63 (dd, J=8.36, 4.25 Hz, 1 H) 7.72 (d, J=8.61 Hz, 2 H) 8.05 (dd, J=8.95, 1.81 Hz, 1 H) 8.10 (d, J=1.96 Hz, 1 H) 8.13-8.19 (m, 1 H) 8.32 (d, J=1.76 Hz, 1 H) 8.47 (d, J=8.51 Hz, 1 H) 8.72 (d, J=1.76 Hz, 1 H) 8.97 (dd, J=4.16, 1.32 Hz, 1 H) 10.32 (s, 1 H)
WORKUP
后处理
- custom) A 15 mL sealed pressure tube
- customThe flask was flushed with argon
- customsealed
- customThe crude mixture was partitioned between water and ethyl acetate
- extractionextracted with ethyl acetate (3×)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- custompurified via ISCO, 40 g RediSep® (Teledyne ISCO, Lincoln, Nebr.) column with a 20-100% gradient of ethyl acetate in hexanes