Acetic Acid → HCID 72721009, compound

Participants

Reaction Steps

16 g (35.3 mmol) of ethyl 2-((6-chloro-3-((3-(trifluoromethyl)phenyl)ethynyl) imidazo[1,2-a]pyridin-2-yl)methylthio)acetate were added to 75 ml of ethanol and 75 ml of tetrahydrofurane before adding 4.24 ml (42.4 mmol) of a 32% sodium hydroxide aqueous solution. The mixture was stirred at r.t. for 2 h, and then 50 ml of water were added after 30 min for solubilising the precipitated solid. The solvent was evaporated in vacuo, the obtained residue was diluted in 250 ml of water and 50 ml of diisopropyl ether, and then the solution was brought to an acid pH by adding 2.53 ml (44.2 mmol) of acetic acid. The precipitated solid was filtered and then washed with water and diisopropyl ether. 12.45 g (yield=83%) of 2-((6-chloro-3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methylthio)acetic acid was obtained as a yellow solid. LC-MS: m/z=425 (MH+) UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 12.65 (s, 1H), 8.96 (s, 1H), 8.19 (s, 1H), 8.03 (d, J=7.6 Hz, 1H), 7.84-7.63 (m, 3H), 7.50 (dd, J=9.5, 1.8 Hz, 1H), 4.07 (s, 2H), 3.40 (s, 2H).

Provenance & Evidence