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Imidazole → (5-Imidazol-1-yl-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone

HRID 2068613
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2068613
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([N:9]2[C@@H:18]3[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C[NH:26][CH2:27][CH2:28][NH:29][CH3:30].N1C=CN=C1>COCCOC.C(Cl)Cl.[Cu]I>[N:26]1([C:2]2[S:6][CH:5]=[C:4]([C:7]([N:9]3[CH:18]4[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]4)[CH2:12][CH2:11][CH2:10]3)=[O:8])[CH:3]=2)[CH:27]=[CH:28][N:29]=[CH:30]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 795ImidazoleHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 86646712HCID 86646712, Verbindung

Produkt 1

HCID 44224463(5-Imidazol-1-yl-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanoneAusbeute 274,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 6344DichloromethaneLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.15 mmol) was added to a solution of potassium carbonate (0.15 mmol), N,N′-dimethylethylene-diamine (0.03 mmol), imidazole (0.3 mmol) and copper (I) iodide (0.03 mmol) in DME (1 mL). The reaction mixture was heated under nitrogen to 120° C. for 90 hours and then diluted with DCM (5 mL) and washed with water. The organic solution was dried and filtered and the solvent evaporated. The residue was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum to give the title compound as a pale brown solid (26 mg). LCMS m/z 316.06 [M+H]+ RT=6.44 min. (Analytical Method 2).

Aufarbeitung

  1. washwashed with water
  2. customThe organic solution was dried
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue was purified by HPLC
  6. washeluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ce5cd0c0457a40aea963f69ade052cb8
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299063B2

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