5-Bromoisoquinoline → N-(tert-butoxycarbonyl)-N-methyl-N'-(5-isoquinolyl)-1,3-propylenediamine

HRID 10508

Reaktionsgleichung

Reaktionsgleichung von HRID 10508
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[C:33]([O:37][C:38](=[O:45])[N:39]([CH2:41][CH2:42][CH2:43][NH2:44])[CH3:40])([CH3:36])([CH3:35])[CH3:34].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:33]([O:37][C:38]([N:39]([CH3:40])[CH2:41][CH2:42][CH2:43][NH:44][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)=[O:45])([CH3:36])([CH3:35])[CH3:34]

Komponenten

6

Edukt 4

HCID 7364875-BromoisoquinolineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 2756543tert-butyl N-(3-aminopropyl)-N-methylcarbamateHCID 23676156Sodium t-butoxide

Produkt 1

HCID 21979883N-(tert-butoxycarbonyl)-N-methyl-N'-(5-isoquinolyl)-1,3-propylenediamineAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (252 mg), tris(dibenzylideneacetone)palladium(0) (59 mg), 2-(di-tert-butylphosphino)biphenyl (74 mg), (3-aminopropyl)methylcarbamic acid tert-butyl ester (274 mg, Asta Tech), and sodium tert-butoxide (163 mg) in toluene was stirred with heating at 70° C. for 3 hours. The reaction mixture was returned to room temperature and purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (325 mg).

Aufarbeitung

  1. customwas returned to room temperature
  2. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-34859159c1f24492b072bc7bfbc36a45
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094789B2

Verknüpfte Notizen

Wird geladen…