Water → 5-Phenylethynyl-2-ureido-thiophene-3-carboxylic Acid Amide

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-ureido-thiophene-3-carboxylic acid amide (0.264 g, 1.0 mmol), copper (I) iodide (0.005 g), triphenyl phosphene (0.030 g, 15 mole %), palladium acetate (0.010 g, 5% mole %), triethyl amine (1 mL) and phenylacetylene (0.1 g, 1.1 mmol) in DMF (4 mL) was added to a 9 mL reaction vial. The reaction vial was sealed and heated to 100° C. in a Smith Microwave Synthesizer for 20 min. Water (5 mL) and ethyl acetate (20 mL) were added to the reaction mixture, the organic phase was separated and then washed with brine (2×10 mL) and water (1×10 mL), and dried over anhydrous magneium sulfate. After filtration, the solvent was removed under vacuum and the crude residue was taken into DMSO (5 mL) and purified utilizing a Gilson preparative HPLC to give the above titled compound as a light brown solid (0.050 g, 0.18 mmol, 18% yield). LC-MS [M+H]+ m/z 286.

Provenance & Evidence