Potassium Carbonate → 1-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-3-pyridin-3-yl-imidazolidin-2-one

HRID 80027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 80027
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:2]=1.Br[C:14]1[S:18][C:17]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:16]=2[C:15]=1[CH3:24].N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:23][C:21]1[CH:20]=[CH:19][C:17]2[S:18][C:14]([N:9]3[CH2:10][CH2:11][N:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[C:8]3=[O:12])=[C:15]([CH3:24])[C:16]=2[CH:22]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 148342041-(Pyridin-3-yl)imidazolidin-2-oneHCID 667212022-Bromo-5-fluoro-3-methylbenzo[b]thiophene

Produkt 1

HCID 596362221-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-3-pyridin-3-yl-imidazolidin-2-oneAusbeute 61,64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions as in Example 1, 1-pyridin-3-yl-imidazolidin-2-one (I-1b: 73 mg, 0.45 mmol) was reacted with 2-bromo-5-fluoro-3-methyl-benzo[b]thiophene (110 mg, 0.45 mmol), 1,4-dioxane (5 mL), copper iodide (8 mg, 0.045 mmol), trans-1,2-diamino cyclohexane (7 mg, 0.0675 mmol) and potassium carbonate (124 mg, 0.9 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform), afforded 90 mg of the product (61.64% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% MeOH in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-c2b6d37cb4cd4610869349b3dc85cf78
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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