反应详情

温度

90 °C

A reaction tube was charged with 2.0 M aqeuous sodium carbonate (199 μL, 397 μmol), PdCl2(dppf)-CH2Cl2 (11 mg, 13 μmol), N-(5-bromo-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamide (50 mg, 132 μmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)cyclohexanecarboxamide (77 mg, 199 μmol) and 0.7 mL dioxane. The tube was purged with argon, sealed and the mixture was heated at 90° C. for 3 h. The reaction mixture was concentrated, dissolved in CH2C2Cl2/MeOH, and purified by silica gel chromatography 0-5% MeOH/CH2Cl2 to provide N-(6-(6-chloro-5-(4-methoxyphenylsulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)cyclohexanecarboxamide (16 mg, 22% yield) as a white solid. This material contained a single impurity and was further purified by reverse phase chromatography, Gilson, 20-90% gradient of 0.1% TFA/ACN in water over 15 min to provide N-(6-(6-chloro-5-(4-methoxyphenylsulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)cyclohexanecarboxamide (16 mg, 22% yield) as a white solid. MS (ESI pos. ion) m/z calc'd for C26H25ClN4O4S2: 557.1/559.1. found 557.0/558.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16-1.51 (m, 6H), 1.73-1.83 (m, 2H), 1.83-1.93 (m, 2H), 2.54-2.62 (m, 1H), 3.83 (s, 3H), 7.07-7.15 (m, 2H), 7.65-7.74 (m, 3H), 7.81-7.88 (m, 1H), 7.99 (s, 1H), 8.32 (s, 1H), 8.61 (s, 1H), 10.23 (s, 1H), 12.39 (s, 1H).

1. customThe tube was purged with argon
2. customsealed
3. concentrationThe reaction mixture was concentrated
4. dissolutiondissolved in CH2C2Cl2/MeOH
5. custompurified by silica gel chromatography 0-5% MeOH/CH2Cl2