2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → [2,6-Dimethyl-4-(6-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-carbamic acid ethyl ester

HRID 2067836

Reaktionsgleichung

Reaktionsgleichung von HRID 2067836
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[K+].Cl.[F:36][C:37]([F:49])([F:48])[C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][CH:47]=1)[CH2:44][NH:43][CH2:42][CH2:41]2.[CH2:50]([O:52][C:53](=[O:64])[NH:54][C:55]1[C:60]([CH3:61])=[CH:59][C:58](Br)=[CH:57][C:56]=1[CH3:63])[CH3:51]>C1(C)C=CC=CC=1>[CH2:50]([O:52][C:53](=[O:64])[NH:54][C:55]1[C:60]([CH3:61])=[CH:59][C:58]([N:43]2[CH2:42][CH2:41][C:40]3[C:45](=[CH:46][CH:47]=[C:38]([C:37]([F:36])([F:48])[F:49])[CH:39]=3)[CH2:44]2)=[CH:57][C:56]=1[CH3:63])[CH3:51]

Komponenten

6

Edukt 4

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 11644748HCID 11644748, VerbindungHCID 217125586-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)HCID 23665647Potassium tert-butoxide

Produkt 1

HCID 58097366[2,6-Dimethyl-4-(6-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-carbamic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Bis(dibenzylidineacetone)palladium (17 mg, 0.03 mmol) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethylamine (35 mg, 0.09 mmol) were added to dry toluene (5 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (166 mg, 1.48 mmol), 6-Trifluoromethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride salt (176 mg, 0.74 mmol) and (4-Bromo-2,6-dimethyl-phenyl)-carbamic acid ethyl ester (200 mg, 0.74 mmol) were then added and the reaction mixture was stirred at 80° C. overnight. The reaction mixture was then cooled to room temperature filtered through silica gel and purified by preparative thin layer chromatography (DCM 100%) to give the desired compound as a solid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 80° C. overnight
  2. filtrationfiltered through silica gel
  3. custompurified by preparative thin layer chromatography (DCM 100%)

Quellen und Nachweise

ORD-Eintrag
ord-be953970d82f45b9bce8a6e4464bb3a0
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293911B2

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