Sodium hydride → 3-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione

HRID 546561

Reaktionsgleichung

Reaktionsgleichung von HRID 546561
[H-].[Na+].[C:3]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N:15]3[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[NH:17][C:16]3=[O:23])[CH:13]=2)[C:8]([CH3:25])([CH3:24])[CH2:7]1)(=[O:5])[CH3:4].[Cl:26][C:27]1[CH:32]=[C:31]([CH2:33]Cl)[CH:30]=[CH:29][N:28]=1>CN(C)C=O.O>[C:3]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N:15]3[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[N:17]([CH2:33][C:31]4[CH:30]=[CH:29][N:28]=[C:27]([Cl:26])[CH:32]=4)[C:16]3=[O:23])[CH:13]=2)[C:8]([CH3:25])([CH3:24])[CH2:7]1)(=[O:5])[CH3:4]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 576259993-(1-Acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethyl-imidazolidine-2,4-dione

Produkt 1

HCID 576259663-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dioneAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To 949 mg of sodium hydride are added dropwise, under argon, 5 mL of dimethylformamide, followed by addition of a solution of 6.8 g of 3-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethylimidazolidine-2,4-dione obtained in stage g) below in 40 mL of dimethylformamide. The solution obtained is stirred for 1.5 hours at 25° C., followed by addition of 5.24 g of 2-chloro-4-chloromethylpyridine obtained in stage b) below. The reaction mixture is stirred at room temperature for 15 hours and diluted with 300 mL of water, and the solid formed is filtered off, washed with three times 20 mL of water and with twice 20 mL of diethyl ether and dried to give 8.8 g of 3-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione in the form of a beige-coloured solid, the characteristics of which are as follows:

Aufarbeitung

  1. customThe solution obtained
  2. stirringThe reaction mixture is stirred at room temperature for 15 hours
  3. customthe solid formed
  4. filtrationis filtered off
  5. washwashed with three times 20 mL of water and with twice 20 mL of diethyl ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f78c8d64115c419ab40bdfdf6b27dc0b
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935819B2

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