反应 #1135886

反应方程式

NaCl

sarcosine methylester hydrochloride

triethylamine

2-(chloromethyl)imidazo[1,2-a]pyridine

→

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

收率 26.0%

溶剂

dimethylformamide

反应条件

后处理

1. 1
   workup.STIRRINGThe mixture was stirred at r.t. for 16 h
2. 2
   浓缩The aqueous phase was concentrated in vacuo
3. 3
   其他The residue was triturated in 75 ml of isopropanol
4. 4
   其他the salts were removed by filtration
5. 5
   浓缩the filtrate was concentrated in vacuo
6. 6
   其他The crude residue was purified by flash chromatography on a silica gel cartridge (eluent

实验过程

0.303 g (1.773 mmol) of 2-(chloromethyl)imidazo[1,2-a]pyridine were dissolved in 15 ml of dimethylformamide with magnetic stirring and then 0.253 g (1.773 mmol) of sarcosine methylester hydrochloride and 0.741 ml (5.32 mmol) of triethylamine were added. The mixture was stirred at r.t. for 16 h, and then treated with 30 ml of a saturated NaCl aqueous solution. The aqueous phase was concentrated in vacuo. The residue was triturated in 75 ml of isopropanol, the salts were removed by filtration and the filtrate was concentrated in vacuo. The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: dichloromethane/methanol, 95/5, v/v). 0.107 g (yield=26%) of methyl 2-((imidazo[1,2-a]pyridin-2-ylmethyl)(methyl)amino)acetate were obtained as a pale yellow oil. LC-MS: m/z=234 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.49 (d, J=6.8 Hz, 1H), 7.79 (s, 1H), 7.47 (d, J=9.0 Hz, 1H), 7.18 (ddd, J=9.0, 6.7, 1.2 Hz, 1H), 6.84 (td, J=6.7, 1.1 Hz, 1H), 3.76 (s, 2H), 3.61 (s, 3H), 2.32 (s, 3H).

来源