Hydrochloric Acid → 2-(3'-Acetylamino-biphenyl-4-yloxymethyl)-thiazole-4-carboxylic acid

Participants

Reaction Steps

A first stock solution was prepared consisting of 2-(4-iodo-phenoxymethyl) -thiazole-4-carboxylic acid ethyl ester (of intermediate 2; 1.56 g, 4 mmol), bis(tri -cyclohexyl-phosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 140 mg, 0.21 mmol), and dioxane (approximately 82 mL). A second stock solution was prepared consisting of potassium carbonate (1.66 g, 12 mmol) and water (approximately 8.2 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-acetamidobenzeneboronic acid (ASDI Incorporated, Newark, Del.; 107 mg, 0.6 mmol). The mixture was heated in a microwave oven at 170 degrees for 25 min. 1 M HCl (0.1 mL) was added to each vial, and the solution were passed through silica gel columns (1 g of silica), and washed with dimethylacetamide (2×1 mL). The solution was evaporated to dryness to give 2-(3′-acetylamino-biphenyl-4-yloxymethyl) -thiazole-4-carboxylic acid. Mass spectrum MH+=369.

Provenance & Evidence