Pyridine → HCID 10684544, compound

Participants

Reaction Steps

To a mixture of 3-(4-t-butylbenzoylamino)thiophene-2-carboxylic acid (8.09 g, 27 mmol) and methylene chloride (135 mL) was added oxalyl chloride (11.8 mL, 135 mmol). The mixture was heated until bubbling began. The reaction was stirred for 2 h without heating. The reaction was concentrated and the residue was dissolved in methylene chloride (135 mL). To this solution was added pyridine (2.2 mL, 27 mmol) and stirred at room temperature for 1 h. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with water (4 times) and brine, MgSO4 dried and concentrated. The residue was chromatographed (10% ethyl acetate/hexanes) to afford the title compound as a solid (7.44 g, 96%); NMR(CDCl3) d 1.37(s, 9H), 7.35(d, J=5.1 Hz, 1H), 7.52(d, J=8.4 Hz, 2H), 7.91(d, J=5.1 Hz, 1H), 8.22(d, J=8.4 Hz, 2H); MS(FD): 285.

Provenance & Evidence