반응 #44238

반응 방정식

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

O-(2-vinyloxy-ethyl)-hydroxylamine

LiHMDS

→

desired product

수율 99.0%

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

수율 99.0%

용매

THF

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched with saturated aqueous NaHCO3
2. 2
   workup.ADDITIONdiluted with EtOAc
3. 3
   세척The organic layer was washed with brine
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타to give the crude material that
8. 8
   기타was purified by silica gel flash column chromatography (100% CH2Cl2 to 1.5% MeOH in CH2Cl2)

실험 절차

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.

출처