Réaction #44185

Équation de réaction

O-(2-Vinyloxy-ethyl)-hydroxylamine

4-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

EDCI

HOBt

Et3N

→

clean desired product

Rendement 52.0%

4-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2-vinyloxyethoxy)-amide

Rendement 52.0%

Solvants

EtOAc

DMF

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter 2 hours
2. 2
   Lavagewashed with saturated NH4Cl solution, saturated NaHCO3 solution and brine
3. 3
   SéchageThe organic layer was dried (MgSO4)
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutrePurification by flash column chromatography (3% MeOH in methylene chloride)

Mode opératoire

A mixture of 4-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (0.120 g, 0.352 mmol), EDCI (0.10 g, 0.53 mmol), and HOBt (0.071 g, 0.53 mmol) in DMF (5 mL) was stirred for 3 hours. O-(2-Vinyloxy-ethyl)-hydroxylamine (0.071 mL, 0.70 mmol) was added followed by Et3N (0.098 mL, 0.70 mmol). After 2 hours, the reaction mixture was diluted with EtOAc and washed with saturated NH4Cl solution, saturated NaHCO3 solution and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography (3% MeOH in methylene chloride) gave 0.078 g (52%) clean desired product.

Source