2-Fluoropyridine → 1'-[(6-Chloro-1-pyridin-2-yl-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

HRID 1865966

Reaktionsgleichung

Reaktionsgleichung von HRID 1865966
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=5[C:20](=[O:27])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].F[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=5[C:20](=[O:27])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 596575991'-[(6-chloro-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

Produkt 1

HCID 596576221'-[(6-Chloro-1-pyridin-2-yl-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4'-piperidin]-3-oneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1′-[(6-chloro-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (prepared according to example 16 above) in dry DMF was added NaH (1 eq) and the reaction mixture stirred at room temperature for 30 min and then treated with 2-fluoropyridine (1.5 eq) and heated at 140° C. under microwave irradiation for 15 min. Purification by preparative HPLC gave the desired product in 38% yield.

Aufarbeitung

  1. temperatureheated at 140° C. under microwave irradiation for 15 min
  2. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3aaa92fa8181497a8e1a6fbfc7d7a13a
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629353B2

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