Tetrahydrofuran → HCID 45804650, compound

Temperature

50 °C

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%).

1. temperaturewas cooled to room temperature
2. concentrationconcentrated
3. customto afford the crude acid chloride
4. additionwas added to the solution
5. temperatureto cool to room temperature
6. custompartitioned between EtOAc and water
7. washThe organic layer was then washed once with of 1M HCl (˜10 mL)
8. dry with materialdried over anhydrous Na2SO4(s)
9. concentrationconcentrated

ORD record

ord-bf20e121d8b045068facd107277bf11a

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383825B2