Реакция #509031

Уравнение реакции

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

Выход 52.0%

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

Выход 52.0%

Растворители

EtOAc

DMF

Условия реакции

Обработка

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

Методика

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.

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