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 (190 mg, 0.607 mmol) and 2-chloro-5-propylpyrimidine (114 mg, 0.728 mmol) in DMF (4 mL) was added K2CO3 (252 mg, 1.820 mmol). Upon completion of addition, the reaction mixture was heated to 100° C., where it stirred overnight. At the conclusion of this period, the reaction mixture was cooled to rt, diluted with water (10 mL) and then extracted with EtOAc (3×10 mL). The combined organic layers were dried (Na2SO4), filtered, and then concentrated to yield the crude product. The crude product was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 30% EtOAc) to afford Compound 1C as a white solid (131 mg, 0.302 mmol, 50% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 8.17 (s, 2H), 7.77 (d, J=1.9 Hz, 1H), 7.51-7.56 (m, 1H), 7.44-7.49 (m, 1H), 5.40-5.49 (m, J=7.9, 7.9, 4.0, 3.9 Hz, 1H), 4.23 (ddd, J=13.4, 6.8, 4.0 Hz, 2H), 3.63-3.73 (m, 2H), 2.42 (t, J=7.6 Hz, 2H), 2.14-2.22 (m, 2H), 1.89-1.99 (m, 2H), 1.56-1.64 (m, 2H), 0.95 (t, J=7.4 Hz, 3H).

Provenance & Evidence