反应 #1135887

反应方程式

methyl 2-((imidazo[1,2-a]pyridin-2-ylmethyl)(methyl)amino)acetate

N-iodosuccinimide

water

→

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

收率 56.4%

溶剂

acetonitrile

反应条件

后处理

1. 1
   萃取extracted with 3×10 ml of ethyl acetate
2. 2
   洗涤The combined organic phases were washed with 20 ml of a saturated NaCl aqueous solution
3. 3
   其他dried on Na2SO4 which
4. 4
   其他was then removed by filtration
5. 5
   浓缩The obtained filtrate was concentrated in vacuo
6. 6
   其他The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: ethyl acetate 100%)

实验过程

0.107 g (0.459 mmol) of methyl 2-((imidazo[1,2-a]pyridin-2-ylmethyl)(methyl)amino)acetate were dissolved in 4 ml of acetonitrile with magnetic stirring, to this solution were added 0.112 g (0.482 mmol) of N-iodosuccinimide. The mixture was stirred at r.t. for 16 h. The reaction mixture was treated with 10 ml of water and then extracted with 3×10 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 flash chromatography on a silica gel cartridge (eluent: ethyl acetate 100%). 0.093 g (yield=46%) of methyl 2-(((3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)(methyl)amino)acetate were obtained as a yellow oil. LC-MS: m/z=360 (MH+); UV purity at 254 nm=82%. 1H NMR (300 MHz, DMSO) δ 8.30 (d, J=6.8 Hz, 1H), 7.54 (d, J=9.0 Hz, 1H), 7.41-7.23 (m, 1H), 7.03 (t, J=6.7 Hz, 1H), 3.79 (s, 2H), 3.62 (s, 3H), 3.37 (s, 2H), 2.34 (s, 3H).

来源