Potassium Carbonate → (1-(5-(4-Methoxypyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone

Participants

Reaction Conditions

Reaction Steps

2-Bromo-4-methoxypyridine (215 mg, 1.145 mmol, 1.1 eq), potassium carbonate (431 mg, 3.124 mmol, 3.0 eq) and PdCl2(dppf) (85 mg, 0.104 mmol, 0.1 eq) were added at room temperature and under an inert atmosphere to a solution of the raw product from 141a) (500 mg, 1.041 mmol, 1.0 eq) in DMF (10 mL). The reaction mixture was stirred at 100° C. for 3 h and then cooled to room temperature. For the work up, the mixture was diluted with ethyl acetate (20 mL), washed with water (2×20 mL) and brine, and dried over anhydrous sodium sulfate. The solvents were removed under reduced pressure and the remnant was purified by column chromatography [100-200 mesh silica gel; 5% methanol in dichloromethane]. White solid. Yield: 200 mg (41% of theory over two steps)

Provenance & Evidence