反应详情

温度

100 °C

To a degassed solution of 6-bromo-2-(piperidin-4-yloxy)benzo[d]thiazole (800 mg, 2.55 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.185 g, 3.83 mmol) and potassium carbonate (1.412 g, 10.22 mmol) in dioxane (21 mL) and water (7 mL) was added Pd(Ph3P)4 (148 mg, 0.128 mmol). The reaction mixture was stirred at 100° C. overnight. The mixture was cooled to rt, diluted with water (60 mL), and extracted with CH2Cl2 (3×30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (silica gel, CH2Cl2-MeOH gradient 0 to 20% MeOH) to afford tert-butyl 4-(2-(piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (923 mg, 2.221 mmol, 87% yield) as a white foam. LCMS (m/z)=416 (M+H)+.

1. temperatureThe mixture was cooled to rt
2. extractionextracted with CH2Cl2 (3×30 mL)
3. dry with materialThe combined organic layers were dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by column chromatography (silica gel, CH2Cl2-MeOH gradient 0 to 20% MeOH)