Water → HCID 90031906, compound

Participants

Reaction Conditions

Reaction Steps

In a flask placed under an argon flow, 0.16 g (0.352 mmol) of methyl 2-((3-((3-(trifluoromethyl)-phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)benzoate were dissolved in 4 ml of tetrahydrofurane with magnetic stirring, the mixture was cooled to 0° C. and then 0.148 ml (0.492 mmol) of RED-Al were added. The mixture was stirred at 0° C. for 15 min before being diluted with 15 ml of ethyl acetate and poured into 20 ml of water. With intense stirring, 1 ml of a NaOH aqueous solution (32% by mass) was slowly added. After separation, the organic phase was washed with 2×10 ml of water. The aqueous phases were extracted with 2×5 ml of ethyl acetate. The combined organic phases were washed with 20 ml of a saturated NaCl aqueous solution and then dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. The crude residue was purified by trituration in 10 ml of diisopropyl ether. The solid was isolated by filtration and dried in vacuo. 0.091 g (yield=58%) of (2-((3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl) methoxy)phenyl)methanol were obtained as a pale brown solid. LC-MS: m/z=425 (M+2H+); UV purity at 254 nm=94%. 1H NMR (300 MHz, DMSO) δ 8.77 (d, J=6.8 Hz, 1H), 8.05 (s, 1H), 7.92 (d, J=7.6 Hz, 1H), 7.73 (dt, J=14.3, 7.8 Hz, 3H), 7.55-7.43 (m, 1H), 7.38 (d, J=7.4 Hz, 1H), 7.20 (d, J=3.6 Hz, 3H), 7.03-6.86 (m, 1H), 5.39 (s, 2H), 4.98 (t, J=5.7 Hz, 1H), 4.55 (d, J=5.6 Hz, 2H).

Provenance & Evidence