Reaction #2358536

Reaction equation

2-Fluoro ethylamine

triethylamine

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

EDCI

→

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

Yield 91.0%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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).

Source