2-Bromo-3-methoxypyridine → HCID 66666788, compound

Participants

Reaction Conditions

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (0.325 g, 0.28 mmol) and 1M aqueous solution of sodium hydrogen carbonate (5.6 mL, 5.6 mmol) were added to 4-(4-chlorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (Preparation 13, 1.0 g, 2.8 mmol) and 2-bromo-3-methoxypyridine (0.528 g, 2.8 mmol) in 1,4-dioxane (30 mL). The mixture was heated at 85° C. for 18 hours under a nitrogen atmosphere, then cooled, diluted with water (30 mL) and extracted with EtOAc (3×30 mL). The organic layer was washed with water (2×30 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford an oil. The crude product was purified by silica gel chromatography eluting with 10 to 80% tert-butyl dimethyl ether in heptane to yield the title compound as a white solid (0.175 g).

Provenance & Evidence