反应 #1135879

反应方程式

(3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl) methanol

sodium hydride

diethylcarbamoyl chloride

→

(3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl)methyl diethylcarbamate

收率 72.1%

溶剂

dimethylformamide

反应条件

后处理

1. 1
   其他The cold bath was withdrawn
2. 2
   workup.STIRRINGthe mixture was stirred at r.t. for 2 h
3. 3
   workup.ADDITIONbefore being treated with 30 ml of a saturated NaCl aqueous solution
4. 4
   萃取The aqueous phase was extracted with 3×10 ml of ethyl acetate
5. 5
   其他The combined organic phases were dried on Na2SO4 which
6. 6
   其他was then removed by filtration
7. 7
   其他The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate, 6/4, v/v)

实验过程

0.1 g (0.403 mmol) of (3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl) methanol were solubilised in 3 ml of dimethylformamide with magnetic stirring. The mixture was cooled to 0° C., 0.048 g (1.208 mmol) of sodium hydride (60% by mass) were added portion wise. The mixture was stirred for 10 min at 0° C. and then 0.204 ml (1.611 mmol) of diethylcarbamoyl chloride were added. The cold bath was withdrawn, the mixture was stirred at r.t. for 2 h before being treated with 30 ml of a saturated NaCl aqueous solution. The aqueous phase was extracted with 3×10 ml of ethyl acetate. The combined organic phases were dried on Na2SO4 which was then removed by filtration. The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate, 6/4, v/v). 0.101 g (yield=72%) of (3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl)methyl diethylcarbamate were obtained as a pale yellow solid. LC-MS: m/z=348 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.61 (d, J=6.8 Hz, 1H), 7.74-7.59 (m, 3H), 7.53-7.38 (m, 4H), 7.13 (td, J=6.8, 1.1 Hz, 1H), 5.30 (s, 2H), 3.22 (q, J=7.1 Hz, 4H), 1.01 (t, J=7.1 Hz, 6H).

来源