1,1,1-Trifluoro-3-iodopropane → 6-[(3,3,3-Trifluoropropyl)sulfanyl]pyridine-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of 6-sulfanylpyridine-3-carboxylic acid (0.5 g, 3.22 mmol) in EtOH (50 mL) at 0 C was added sodium acetate (0.26 g, 3.22 mmol) and 1,1,1-trifluoro-3-iodopropane (0.72 g, 3.22 mmol) and the mixture was heated at 80 C for 24 h. The mixture was concentrated under vacuum, water was added and the mixture was acidified to pH 4 using acetic acid. The resultant yellow precipitate was collected by filtration and purified by FCC, eluting with 2% MeOH in DCM to afford the title compound (0.459 g, 57%). Method B HPLC-MS: MH+ requires m/z=252 Found: m/z=252, Rt=1.84 min (91%).

Provenance & Evidence