Potassium Carbonate → N-(2-Amino-2-oxoethyl)-1-(5-(4-methoxypyridin-2-yl)pyrimidin-2-yl)-N-methyl-3-(methylthio)-1H-indole-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

PdCl2(dppf) (0.094 g, 0.115 mmol) was added under an argon atmosphere to a suspension of N-(2-amino-2-oxo ethyl)-1-(5-bromopyrimidin-2-yl)-N-methyl-3-(methylthio)-1H-indole-6-carboxamide (1.0 g, 2.3 mmol), bis(pinacolato)diboron (0.655 g, 2.58 mmol) and potassium acetate (0.68 g, 6.91 mmol) in dioxane (40 mL) and the mixture was stirred at 110° C. for 1 h. After cooling to room temperature, 2-bromo-4-ethoxy-pyridine (0.65 g, 3.45 mmol), a 2M potassium carbonate solution (8.0 mL) and tetrakis(triphenylphosphine)palladium(0) (0.133 g, 0.115 mmol) were added. The reaction mixture was stirred at 100° C. for 16 h, and then filtered through celite. The filter was washed with methanol/dichloromethane (1:9), the filtrate was concentrated and the residue purified by flash column chromatography [silica; methanol/dichloromethane=3.5:96.5]. White solid. Yield: 0.185 g

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