反应 #1135872

反应方程式

2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl) methoxy)acetic acid

sulfuric acid

isopropanol

→

isopropyl 2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)-methoxy)acetate

收率 91.0%

反应条件

后处理

1. 1
   洗涤The reaction medium was washed with 2×10 ml of water
2. 2
   萃取extracted with 2×30 ml of ethyl acetate
3. 3
   洗涤The combined organic phases were washed with 30 ml of a saturated NaCl aqueous solution
4. 4
   其他dried on Na2SO4 which
5. 5
   其他was then removed by filtration
6. 6
   浓缩The obtained filtrate was concentrated in vacuo

实验过程

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).

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