Water → HCID 118195069, compound

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, 200 mg (0.446 mmol) of ethyl 2-((3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methylthio)-acetate were dissolved in 4 ml of tetrahydrofurane and 33.9 mg (0.892 mmol) of LiAlH4 were added. The solution was heated to 50° C. for 1 h. 0.030 ml of water were slowly added, followed by the addition of 0.030 ml of 6N sodium hydroxide and then with 0.1 ml of water. After 30 min of stirring, the precipitate was filtered, and washed with ethyl acetate. The collected organic phases were washed with brine and then dried on Na2SO4 which was then removed by filtration and the obtained filtrate was concentrated in vacuo. The obtained solid was triturated in ethyl acetate, filtered and then washed with ethyl acetate. 50 mg (yield=28%) of 2-((3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)-methylthio) ethanol were obtained as a white solid. LC-MS: m/z=407 (MH+) UV purity at 254 nm=89%. 1H NMR (300 MHz, DMSO) δ 8.30 (d, 1H), 8.12 (s, 1H), 7.99 (m, 1H), 7.75 (m, 2H), 7.03 (m, 1H), 6.88 (d, 1H), 4.84 (t, 1H), 3.96 (s, 5H), 3.60 (m, 2H), 2.67 (t, 2H).

Provenance & Evidence