Réaction #44238

Équation de réaction

methyl 4-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate

O-(2-vinyloxy-ethyl)-hydroxylamine

LiHMDS

→

desired product

Rendement 99.0%

4-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridazine-3-carboxamide

Rendement 99.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was quenched with saturated aqueous NaHCO3
2. 2
   workup.ADDITIONdiluted with EtOAc
3. 3
   LavageThe organic layer was washed with brine
4. 4
   Séchagedried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   Autreto give the crude material that
8. 8
   Autrewas purified by silica gel flash column chromatography (100% CH2Cl2 to 1.5% MeOH in CH2Cl2)

Mode opératoire

To a solution of methyl 4-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate (25 mg, 0.077 mmol) and O-(2-vinyloxy-ethyl)-hydroxylamine (24 mg, 0.23 mmol) in THF (2 mL) at 0° C. was added LiHMDS (0.54 mL, 0.54 mmol, 1 M in THF). The reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was quenched with saturated aqueous NaHCO3 and diluted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (100% CH2Cl2 to 1.5% MeOH in CH2Cl2) to afford 30 mg (99%) of the desired product.

Source