Potassium Carbonate → HCID 66666696, compound

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (0.232 g, 1.68 mmol) and (2-methoxypyridin-3-yl)boronic acid (0.215 g, 1.26 mmol) were added to a solution of 3-bromo-4-(4-chloro-2-methoxyphenoxy)benzonitrile (Preparation 3, 0.284, 0.839 mmol) in dioxane (10 mL). The reaction was degassed three times, then tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol) was added and the mixture was degassed three further times. The resulting mixture was heated at 70° C. over for 72 hours, then the reaction was cooled to room temperature. Then (2-methoxypyridin-3-yl)boronic acid (0.072 g, 0.42 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol) were added and the reaction was heated at 90° C. for 3 hours. The reaction was allowed to cool to room temperature and the solvent removed in vacuo to give a black oil which was absorbed onto silica and purified by silica gel chromatography (Biotage®, SNAP cartridge 50 g, DCM 6CV then 99/1, DCM/MeOH 5 CV and then 9/1, DCM/MeOH 6 CV) to afford the title compound as a white solid (0.265 g).

Provenance & Evidence