Tetrahydrofuran → HCID 45804650, compound

Participants

Reaction Conditions

Reaction Steps

A dry 25 mL flask was charged with 3-methylthiophene-2-carboxylic acid (0.201 g, 1.41 mmol) followed by thionyl chloride (10 mL). The reaction was heated to 50° C. for 2 h after which the reaction was cooled to room temperature and concentrated to afford the crude acid chloride. The crude acid chloride was dissolved into 10 mL of THF and 3-ethynyl-phenylamine (0.165 g, 1.41 mmol) was added to the solution followed by NEt3, and the mixture was allowed to stir at 55° C. for 4 hours. The reaction mixture was allowed to cool to room temperature and then partitioned between EtOAc and water. The organic layer was then washed once with of 1M HCl (˜10 mL) and then twice with of saturated aqueous NaHCO3 (˜10 mL) The organic extracts were combined, dried over anhydrous Na2SO4(s) and then concentrated to give the title compound as a tan solid (265 mg, 1.10 mmol, 78%).

Provenance & Evidence