Réaction #44252

Équation de réaction

lithium bis(trimethylsilyl)amide

2-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridine-3-carboxamide

methyl 2-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate

O-(2-vinyloxy-ethyl)-hydroxylamine

→

pure desired product

Rendement 94.0%

2-(4-Bromo-2-fluorophenylamino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Rendement 94.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was warmed to room temperature
2. 2
   Autrewas quenched by the addition of saturated NaHCO3
3. 3
   Autrepartitioned between EtOAc and saturated NaCl
4. 4
   AutreThe layers were separated
5. 5
   Séchagethe organic layer was dried (Na2SO4)
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutrePurification by flash column chromatography (methylene chloride/MeOH, 20:1)

Mode opératoire

Preparation of 2-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridine-3-carboxamide: To a solution of methyl 2-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate (0.060 g, 0.16 mmol) in THF (2 mL) was added O-(2-vinyloxy-ethyl)-hydroxylamine (0.042 ml, 0.41 mmol). The solution was cooled to 0° C. and lithium bis(trimethylsilyl)amide (0.81 ml, 0.81 mmol, 1 M solution in hexanes) was added dropwise. The reaction mixture was warmed to room temperature. After stirring for 35 minutes the reaction mixture was quenched by the addition of saturated NaHCO3 and partitioned between EtOAc and saturated NaCl. The layers were separated and the organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by flash column chromatography (methylene chloride/MeOH, 20:1) gave 0.067 g (94%) pure desired product as an off-white crystalline solid.

Source