6-Chloro-1,2,3,4-Tetrahydroisoquinoline Hydrochloride → n-[4-(6-Chloro-3,4-dihydro-1h-isoquinolin-2-yl)-2,6-dimethyl-phenyl]-3,3-dimethylbutanamide

HRID 2067800

Reaktionsgleichung

Reaktionsgleichung von HRID 2067800
CC(C)([O-])C.[K+].Cl.[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][NH:14][CH2:13][CH2:12]2.Br[C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[C:22]([CH3:35])[CH:21]=1>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[C:22]([CH3:35])[CH:21]=1)[CH2:13][CH2:12]2

Komponenten

5

Edukt 3

HCID 125950846-Chloro-1,2,3,4-Tetrahydroisoquinoline HydrochlorideHCID 23665647Potassium tert-butoxideHCID 59741059N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide

Produkt 1

HCID 24937081n-[4-(6-Chloro-3,4-dihydro-1h-isoquinolin-2-yl)-2,6-dimethyl-phenyl]-3,3-dimethylbutanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Bis(dibenzylidineacetone)palladium (2 mg, 0.0035 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (3.3 mg, 0.0084 mmol) were added to dry toluene (5 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (188 mg, 1.7 mmol), 6-chloro-1,2,3,4-tetrahydro isoquinoline hydrochloride salt (165 mg, 0.8 mmol), and N-(4-bromo-2,6-dimethylphenyl)-3,3-dimethylbutanamide (200 mg, 0.67 mmol) were then added, and the reaction mixture was stirred at 80° C. overnight. The reaction mixture was then cooled to room temperature and filtered through silica gel. Purification by preparative thin layer chromatography afforded the title compound as a solid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 80° C. overnight
  2. filtrationfiltered through silica gel
  3. customPurification by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bc427e67991e46fc9864c55d6304a096
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293911B2

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