Dimethylformamide → HCID 57566815, Verbindung

HRID 1819344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1819344
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]2[CH2:21][NH:20][C:19](=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:24]1[CH:25]=[C:26]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:28][CH:29]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C=O)C>[Cu]I.O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]2[CH2:21][N:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=3)[C:19](=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 125741-Iodo-3-nitrobenzeneHCID 62657Potassium Phosphate, TribasicHCID 145371514-[3-(Benzyloxy)-4-methoxyphenyl]pyrrolidin-2-one

Produkt 1

HCID 57566815HCID 57566815, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a round bottom flask was added 4-(3-benzyloxy-4-methoxyphenyl)-pyrrolidin-2-one (1.76 g, 5.9 mmol), 3-iodonitrobenzene (2.64 g, 10.6 mmol), K3PO4 (2.79 g, 13 mmol), trans-cyclohexanediamine (50 μL), DMF (8 mL) and dioxane (8 mL). The mixture was stirred under N2 for 5 min before the addition of CuI (150 mg). After heating to 110° C. for 20 h, the mixture was cooled to r.t. After filtration, the reaction mixture was diluted with EtOAc (100 mL), washed with saturated NH4Cl, brine and dried over Na2SO4. Concentration and purification by column chromatography on silica gel (EtOAc:hexane=1:3) gave 1.4 g of the desired product. Yield: 57%.

Aufarbeitung

  1. temperaturethe mixture was cooled to r.t
  2. filtrationAfter filtration
  3. additionthe reaction mixture was diluted with EtOAc (100 mL)
  4. washwashed with saturated NH4Cl, brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration and purification by column chromatography on silica gel (EtOAc:hexane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-264eda41177140659e93766d32a0870e
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601742B2

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