Water → 7-bromo-3-(3-chlorophenyl)-2-methylisoquinolin-1(2H)-one

HRID 77389

Reaktionsgleichung

Reaktionsgleichung von HRID 77389
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[H-].[Na+].[N+]([C:25]1C=CC(S(OC)(=O)=O)=CC=1)([O-])=O.O>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[N:8]([CH3:25])[C:9]2=[O:12])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 22582Benzenesulfonic acid, 4-nitro-, methyl esterHCID 24758Sodium hydrideHCID 699288937-bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one2×

Produkt 1

HCID 699285487-bromo-3-(3-chlorophenyl)-2-methylisoquinolin-1(2H)-oneAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7-Bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one (Intermediate 23A) (0.1 g, 0.299 mmol) was dissolved in THF (4 mL), under an atmosphere of nitrogen. Sodium hydride (0.018 g, 0.448 mmol) was added and reaction stirred for 30 minutes. The reaction was then cooled using an ice bath and methyl 4-nitrobenzenesulfonate (0.065 g, 0.299 mmol) was added. The reaction was allowed to warm to room temperature and left to stir overnight. Water was added to the reaction mixture and extracted with EtOAC (×2). The organics were combined and washed with brine, dried (MgSO4) filtered and concentrated under reduced pressure. The mixture was purified on silica (25 g column on Isolera 4) eluting with 0-10% methanol in dichloromethane to afford 7-bromo-3-(3-chlorophenyl)-2-methylisoquinolin-1(2H)-one (51 mg, 0.15 mmol).

Aufarbeitung

  1. customreaction
  2. temperatureThe reaction was then cooled
  3. waitleft
  4. stirringto stir overnight
  5. extractionextracted with EtOAC (×2)
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe mixture was purified on silica (25 g column on Isolera 4)
  11. washeluting with 0-10% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-d964deca7655450c9db475cc20959061
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841289B2

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