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Tris(1,1-dimethylethyl)phosphine → HCID 178419024, Verbindung

HRID 10556
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 10556
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH3:12])=[CH:5][N:6]=[CH:7]2.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[C:26]([O:30][C:31]([NH:33][C@H:34]1[CH2:39][CH2:38][C@@H:37]([NH2:40])[CH2:36][CH2:35]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].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:26]([O:30][C:31]([NH:33][C@H:34]1[CH2:35][CH2:36][C@@H:37]([NH:40][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[C:4]([CH3:12])=[CH:5][N:6]=[CH:7]3)[CH2:38][CH2:39]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 219798825-Bromo-4-methylisoquinoline2×HCID 23676156Sodium t-butoxideHCID 178418966HCID 178418966, Verbindung

Produkt 1

HCID 178419024HCID 178419024, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

According to the method of Example 15, Step A, the title compound was synthesized from Intermediate 93. That is, under nitrogen atmosphere, a suspension of Intermediate 93 (602 mg), tris(dibenzylideneacetone)dipalladium(0) (124 mg), tri(tert-butyl)phosphine (0.5 ml, Kanto Chemicals), cis-N-(tert-butoxycarbonyl)-1,4-cyclohexanediamine (697 mg) and sodium tert-butoxide (390 mg) in toluene was stirred with heating at 120° C. for 16.5 hours. The reaction mixture was cooled to room temperature and added with ethyl acetate (10 ml), and 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=1:1) to obtain the title compound (45 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=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2ef5bc5c67c04ed392a15b43bd1a3710
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07094789B2

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