1,2-Dimethoxyethane → 5-Bromo-2-(4-(phenylsulfonyl)phenyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A 100 ml, pressure vessel was charged with 4,4,5,5-tetramethyl-2-(4-(phenylsulfonyl)phenyl)-1,3,2-dioxaborolane (1.00 g, 2.91 mmol), 2,5-dibromopyridine (0.860 g, 3.63 mmol, Sigma-Aldrich, St. Louis, Mo.), potassium carbonate (1.20 g, 8.72 mmol), tetrakis(triphenylphosphine)palladium (0) (0.168 g, 0.145 mmol, Strem Chemical Inc, Newburyport, Mass.), 16 mL of 1,2-dimethoxyethane, and 4 mL of water. The vessel was sealed and the reaction was heated at 100° C. for 2 h. After cooling to room temperature, the mixture was diluted with EtOAc (30 mL), separated, dried (MgSO4) and concentrated to give an oil. Purification via column chromatography (40 g of silica gel, 0 to 50% EtOAc in hexanes) produced a yellow solid that was slurried with cold (0° C.) MeOH (20 mL) to give 5-bromo-2-(4-(phenylsulfonyl)phenyl)pyridine (0.450 g).

Provenance & Evidence