Reaktion #44185

Reaktionsgleichung

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

Ausbeute 52.0%

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

Ausbeute 52.0%

Lösungsmittel

EtOAc

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle