반응 #44252

반응 방정식

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

수율 94.0%

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

수율 94.0%

용매

THF

반응 조건

후처리

1. 1
   온도The reaction mixture was warmed to room temperature
2. 2
   기타was quenched by the addition of saturated NaHCO3
3. 3
   기타partitioned between EtOAc and saturated NaCl
4. 4
   기타The layers were separated
5. 5
   건조the organic layer was dried (Na2SO4)
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification by flash column chromatography (methylene chloride/MeOH, 20:1)

실험 절차

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.

출처