反应 #1135888

反应方程式

methyl 2-(((3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)(methyl)amino)acetate

3-trifluoromethylphenylacetylene

triethylamine

→

methyl 2-(methyl((3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methyl)amino)acetate

收率 58.8%

溶剂

dimethylformamide

ethyl acetate

反应条件

后处理

1. 1
   其他In a flask placed under an argon
2. 2
   workup.ADDITIONTo this solution, were added
3. 3
   其他The reaction medium was degassed with argon for 10 min
4. 4
   workup.ADDITIONbefore being treated
5. 5
   洗涤washed with 2×15 ml of a saturated NaCl aqueous solution
6. 6
   萃取The aqueous phase was extracted with 20 ml of ethyl acetate
7. 7
   其他The combined organic phases were dried on Na2SO4 which
8. 8
   其他was then removed by filtration
9. 9
   浓缩The obtained filtrate was concentrated in vacuo
10. 10
    其他The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: ethyl acetate 100%)

实验过程

In a flask placed under an argon flow, 0.093 g (0.212 mmol) of methyl 2-(((3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)(methyl)amino)acetate were dissolved in 0.5 ml of dimethylformamide with magnetic stirring. To this solution, were added: 0.004 g (0.021 mmol) of copper iodide, 0.037 ml (0.255 mmol) of 3-trifluoromethylphenylacetylene and 0.444 ml (3.18 mmol) of triethylamine. The reaction medium was degassed with argon for 10 min before adding 0.019 g (0.021 mmol) of Pd2(dba)3. The mixture was stirred at r.t. for 16 h before being treated, diluted with 15 ml of ethyl acetate and washed with 2×15 ml of a saturated NaCl aqueous solution. The aqueous phase was extracted with 20 ml of ethyl acetate. The combined organic phases were dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: ethyl acetate 100%). 0.05 g (yield=57%) of methyl 2-(methyl((3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methyl)amino)acetate were obtained as a pale brown solid. LC-MS: m/z=402 (MH+); UV purity at 254 nm=96%. 1H NMR (300 MHz, DMSO) δ 8.75 (d, J=6.7 Hz, 1H), 8.11 (s, 1H), 7.97 (d, J=7.6 Hz, 1H), 7.83-7.59 (m, 3H), 7.55-7.37 (m, 1H), 7.14 (td, J=6.8, 0.9 Hz, 1H), 3.97 (s, 2H), 3.58 (s, 3H), 3.43 (s, 2H), 2.39 (s, 3H).

来源