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

HRID 880674

Reaktionsgleichung

Reaktionsgleichung von HRID 880674
CNC.CC(C)([O-])C.[K+].Cl.[Cl:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH2:18][NH:17][CH2:16][CH2:15]2.Br[C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([NH:30][C:31](=[O:37])[CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[C:25]([CH3:38])[CH:24]=1>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH2:18][N:17]([C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([NH:30][C:31](=[O:37])[CH2:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[C:25]([CH3:38])[CH:24]=1)[CH2:16][CH2:15]2

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 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′-dicyclohexylphosphanyl-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-acc41914cd3f4b08bc453d2c44301d73
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993593B2

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