反应 #730229

反应方程式

2-Fluoro ethylamine

triethylamine

3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid

EDCI

→

3-(5-dimethylcarbamoyl-pent-1-ynyl)-N-(2-fluoro-ethyl)benzamide

收率 91.0%

溶剂

dichloromethane

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture stirred at room temperature for 16 hrs
2. 2
   洗涤The reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL)
3. 3
   其他The organic layer was separated
4. 4
   干燥dried over magnesium sulfate
5. 5
   其他the solvent evaporated under vacuum
6. 6
   其他The residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient)

实验过程

To a solution of 3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid (0.100 g, 0.38 mmol) in dry dichloromethane (1.5 mL) under a nitrogen atmosphere at room temperature, EDCI (0.0728 g, 0.38 mmol) was added followed by triethylamine (0.162 mL, 1.14 mmol), the resulting mixture was stirred at room temperature for further 5 minutes. 2-Fluoro ethylamine (0.189 g, 1.9 mmol) was then added and the mixture stirred at room temperature for 16 hrs. The reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL) followed by saturated brine solution (100 mL). The organic layer was separated and dried over magnesium sulfate and the solvent evaporated under vacuum. The residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient) to afford 3-(5-dimethylcarbamoyl-pent-1-ynyl)-N-(2-fluoro-ethyl)benzamide (26)(0.103 g, 0.34 mmol, 91% yield).

来源