Dichloromethane → 4-chloro-2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 80832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 80832
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:18]=[C:17](O)[C:16]2[C:15](=[O:20])[N:14]([C:21]3[CH:26]=[C:25]([CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:22]=3[CH3:30])[CH2:13][CH2:12][C:11]=2[N:10]=1.C(=O)(O)[O-].[Na+].[OH-].[Na+].C(Cl)[Cl:39]>>[Cl:39][C:17]1[C:16]2[C:15](=[O:20])[N:14]([C:21]3[CH:26]=[C:25]([CH:27]([CH3:28])[CH3:29])[CH:24]=[CH:23][C:22]=3[CH3:30])[CH2:13][CH2:12][C:11]=2[N:10]=[C:9]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[CH:18]=1

Komponenten

5

Edukt 4

HCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 178424916HCID 178424916, Verbindung

Produkt 1

HCID 712406884-chloro-2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Versuchsvorschrift

To a solution of crude 2-(2,6-dimethylphenyl)-4-hydroxy-6-(5-isopropyl-2-methylphenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (1.4 g, 3.50 mmol) in DCM (35.0 mL) was added Vilsmeier's reagent (0.895 g, 6.99 mmol) as a solid in one portion and the reaction mixture stirred at room temperature. After 2 h 500 mg of Vilsmeier's reagent was added and stirring continued. After 35 min an additional portion of 200 mg of Vilsmeier's reagent was added and stirring continued. After 15 min the reaction mixture was diluted with DCM and poured into saturated aqueous sodium bicarbonate solution containing 1 N NaOH. The layers were separated and the aqueous layer was extracted with DCM (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by FCC (0-20% EtOAc/heptane) to provide 4-chloro-2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one. MS (ESI+) m/z 419.2 (M+H)+.

Aufarbeitung

  1. stirringstirring
  2. stirringstirring
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (2×)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by FCC (0-20% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-57205eddb6134223b537e15bd08efcfa
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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