4-Fluorothieno[2,3-c]pyridine-2-carboxylic acid → 4-Fluorothieno[2,3-c]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluorothieno[2,3-c]pyridine-2-carboxylic acid (765 mg, 3.88 mmol) and copper powder (629 mg, 9.91 mmol) in diphenyl ether (3.8 mL) was heated to boiling for ˜5 min. After cooling to 40° C., the reaction mixture was diluted with heptane (10 mL), filtered through a short pad of Celite, and concentrated to remove the heptane. Purification of the residue by ISCO chromatography (5 to 45% ethyl acetate:heptane) afforded 441 mg (74%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.96 (d, J=1.8 Hz, 1 H), 8.34 (d, J=2.0 Hz, 1 H), 7.61-7.88 (m, 1 H), 7.38-7.57 (m, 1 H); MS (ESI): 154.07 [M+H]+; HPLC tR=2.97 min (ZQ3, polar—4 min).

Provenance & Evidence