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N-BOC-ethylenediamine → N-(tert-butoxycarbonyl)-N'-(5-isoquinolyl)ethylenediamine

HRID 10505
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 10505
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:43])[NH:39][CH2:40][CH2:41][NH2:42])([CH3:36])([CH3:35])[CH3:34].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[C:33]([O:37][C:38]([NH:39][CH2:40][CH2:41][NH:42][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:43])([CH3:36])([CH3:35])[CH3:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 187201N-BOC-ethylenediamineHCID 7364875-BromoisoquinolineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxide

Produkt 1

HCID 21979917N-(tert-butoxycarbonyl)-N'-(5-isoquinolyl)ethylenediamineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 1140TolueneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (416 mg, Spex), tris(dibenzylideneacetone)dipalladium(0) (92 mg), 2-(di-tert-butylphosphino)biphenyl (119 mg), N-(2-aminoethyl)carbamic acid tert-butyl ester (385 mg) and sodium tert-butoxide (269 mg) in toluene (5 ml) was stirred with heating at 80° C. for 2 hours. The reaction mixture was cooled to room temperature and added with ethyl acetate (5 ml). The insoluble matters were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (402 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe insoluble matters were removed by filtration through Celite
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-236c7339795b45e393f5e303add9f945
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07094789B2

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