Reaktion #42085

Reaktionsgleichung

product

N-[3-Acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

MeMgBr

→

9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-2,4,4,6-tetramethyl-4,6-dihydro-5H-[1,3]oxazino[5,4-c]-1,8-naphthyridin-5-one

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 10 min the reaction was quenched with saturated aqueous NH4Cl
2. 2
   workup.ADDITIONdiluted with EtOAc
3. 3
   WaschenThe solution was washed with 10% aqueous NaHSO4
4. 4
   Trocknenbefore drying (Na2SO4)
5. 5
   SonstigeThe concentrated residue was purified by preparative TLC (silica gel)
6. 6
   Wascheneluted with 15% EtOAc in hexane affording the title compound

Vorschrift

To the product of Example 1 (59.5 mg) in THF (2 mL) at 0° C. was added 0.52 mL MeMgBr solution (1.4 M, 75% toluene/25% THF). After 10 min the reaction was quenched with saturated aqueous NH4Cl and then diluted with EtOAc. The solution was washed with 10% aqueous NaHSO4 followed by aqueous NaHCO3/NaOH (4:1) before drying (Na2SO4). The concentrated residue was purified by preparative TLC (silica gel) eluted with 15% EtOAc in hexane affording the title compound. HPLC/MS: 512.0 (M+1), 514.0 (M+3); Rt=5.14 min.

Quelle