Potassium Carbonate → 3-(3'-Carbamoyl-biphenyl-4-yloxymethyl)-benzoic acid

Participants

Reaction Steps

A first stock solution was prepared consisting of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (of Intermediate 1; 1.11 g, 3 mmol), bis(tri-cyclohexyl-phosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 105 mg, 0.16 mmol), and dioxane (approximately 62 mL). A second stock solution was prepared consisting of potassium carbonate (1.245 g, 9 mmol) and water (approximately 6.2 mL). The solutions were sonicated and degassed by bubbling nitrogen gas through them. 4 mL of the first stock solution and 0.4 mL of the second stock solution were added to a reaction vial containing (3-aminocarbonylphenyl)boronic acid (available from Apollo Scientific Ltd., Stockport, UK; 99 mg, 0.6 mmol). The mixture was heated in a microwave oven at 170 degrees for 25 min and then passed through a silica gel column (1 g of silica), and washed with dioxane (1 mL) and dimethylacetamide (1 mL). 2 M potassium hydroxide solution (0.4 mL) was added. The mixture was stirred at room temperature overnight, and then 1 M HCl (0.8 mL) was added and the solvents were removed in the Genevac. Aqueous methanol (50%; approximately 2 mL) was added, then the vial was centrifuged and the solvent was removed. This process was repeated to give 3-(3′-carbamoyl-biphenyl-4-yloxymethyl)-benzoic acid. Mass spectrum MH+=348.

Provenance & Evidence