Sulfuric Acid → HCID 73051806, compound

Participants

Reaction Conditions

Reaction Steps

0.155 g (0.478 mmol) of 2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl) methoxy)acetic acid were solubilized with magnetic stirring in 5 ml of isopropanol and a drop of sulfuric acid was added. The mixture was stirred at 60° C. for 3 h. The reaction medium was washed with 2×10 ml of water, and then extracted with 2×30 ml of ethyl acetate. The combined organic phases were washed with 30 ml of a saturated NaCl aqueous solution, dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. 0.162 mg (yield=91%) of isopropyl 2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)-methoxy)acetate were obtained as a brown oil. LC-MS: m/z=367 (MH+); UV purity at 254 nm=98%. 1H NMR (300 MHz, DMSO) δ 8.62 (d, J=6.8 Hz, 1H), 7.74 (dd, J=8.7, 5.5 Hz, 2H), 7.67 (d, J=9.0 Hz, 1H), 7.45 (d, J=7.0 Hz, 1H), 7.33 (t, J=8.9 Hz, 2H), 7.12 (t, J=6.5 Hz, 1H), 4.93 (dt, J=12.5, 6.3 Hz, 1H), 4.78 (s, 2H), 4.19 (s, 2H), 1.15 (d, J=6.3 Hz, 6H).

Provenance & Evidence