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

HRID 10505

Reaktionsgleichung

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]

Komponenten

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

temperatureThe reaction mixture was cooled to room temperature
customThe insoluble matters were removed by filtration through Celite
customThe solvent was evaporated under reduced pressure
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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