Sodium Carbonate → HCID 58765697, compound

Participants

Reaction Conditions

Reaction Steps

3-[2-Methyl-4-(2-(5-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiazol-4-yl)-propoxy)-phenyl]-propionic acid methyl ester (5.2 g, 6.92 mmol) is dissolved in anhydrous toluene (30 mL), degassed, and filled with nitrogen three times. [1,1′-Bis-(diphenylphosphino)ferrocene]dichloropalladium(II) (330 mg, 0.346 mmol), 2-bromopyrimidine (2.24 g, 14 mmol), and sodium carbonate (3.71 g in 5 mL water, 35 mmol) are added, and the degassing procedure is repeated. The reaction is heated to 100° C. and monitored by HPLC. Upon complete consumption of starting material, the reaction is allowed to cool to room temperature and diluted with ethyl acetate. Celite is added and the mixture is filtered and rinsed with more ethyl acetate and water. The solution is further diluted with water and the two phases are separated. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The pure 3-(2-Methyl-4-{2-[5-methyl-2-(4-pyrimidin-2-yl-phenyl)-thiazol-4-yl]-propoxy}-phenyl)-propionic acid methyl ester (1.3 g, 2.87 mmol) is obtained after column chromatography (65% yield).

Provenance & Evidence