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HCID 86684795, Verbindung → HCID 86684797, Verbindung

HRID 1527970
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1527970
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[N:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[I-].[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([Zn+])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C)C(=O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:11]=[C:10]([C:12]1[CH:17]=[CH:16][N:15]=[N:14][CH:13]=1)[CH2:9][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([CH:36]2[CH2:37][CH2:38][N:33]([C:31]([O:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:32])[CH2:34][CH2:35]2)=[CH:7][CH:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 86684795HCID 86684795, VerbindungHCID 178452044HCID 178452044, Verbindung

Produkt 1

HCID 86684797HCID 86684797, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator2×
HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
2×
HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a yellow solution of 3-(4-bromophenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one (example 2, step 3; 180 mg, 472 μmol) in N,N-dimethylacetamide (4 mL) were added copper(I) iodide (9 mg, 47 μmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (17.3 mg, 23.6 μmol) and (1-(tert-butoxycarbonyl)piperidin-4-yl)zinc(II) iodide solution (0.5 M in N,N-dimethylacetamide, 1.9 mL, 0.95 mmol; J. Org. Chem. 2004, 69, 5120). The reaction mixture was heated at 85° C., then after 5 h another portion of copper(I) iodide (9 mg, 47 μmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (17.3 mg, 23.6 μmol) was added, then after 1 h the reaction mixture was partitioned between sat, aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. The residue was suspended in ethyl acetate/heptane 1:1 and insoluble material was removed by filtration. The filtrate was purified by chromatography (SiO2; ethyl acetate/heptane 1:1) to produce the title compound (66 mg, 29%). Orange foam, MS: 486.4 [M+H]+.

Aufarbeitung

  1. customafter 1 h the reaction mixture was partitioned
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customwas removed by filtration
  7. customThe filtrate was purified by chromatography (SiO2; ethyl acetate/heptane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0b296b37ae9c4bd7813dadae67a96bcd
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090565B2

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