反応 #2358536

反応方程式

2-Fluoro ethylamine

triethylamine

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

EDCI

→

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

収率 91.0%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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 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).

出典