Potassium Carbonate → 6-Bromo-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-2-(piperidin-4-yloxy)benzo[d]thiazole (10 g, 31.9 mmol) and 2-chloro-5-propylpyrimidine (7.5 g, 47.9 mmol) in DMF (150 mL) was added potassium carbonate (17.65 g, 128 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was cooled to rt, diluted with water (300 mL) and extracted with EtOAc (3×150 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The crude product was purified by chromatography (silica gel, hexanes-EtOAc gradient 0 to 50% EtOAc) to afford 6-bromo-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole (11.9 g, 27.5 mmol, 86% yield) as a white solid. 1H NMR (500 MHz, chloroform-d) δ ppm 8.17 (2H, s), 7.77 (1H, d, J=1.9 Hz), 7.52-7.55 (1H, m), 7.45-7.49 (1H, m), 5.41-5.49 (1H, m), 4.23 (2H, ddd, J=13.4, 6.8, 4.0 Hz), 3.62-3.74 (2H, m), 2.42 (2H, t, J=7.6 Hz), 2.14-2.23 (2H, m), 1.89-1.99 (2H, m), 1.56-1.63 (2H, m), 0.95 (3H, t, J=7.4 Hz).

Provenance & Evidence