Sodium Carbonate → (6-Dibenzofuran-4-yl-pyrimidin-4-yl)-(2-methyl-5-nitro-phenyl)-amine

HRID 1360349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360349
C([O-])([O-])=O.[Na+].[Na+].Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=2[CH3:24])[CH:9]=1.[CH:25]1[C:33]2[C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[O:30][C:29]=2[C:28](B(O)O)=[CH:27][CH:26]=1>>[CH:25]1[C:33]2[C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[O:30][C:29]=2[C:28]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=3[CH3:24])[CH:9]=2)=[CH:27][CH:26]=1

Komponenten

4

Edukt 3

HCID 10340Sodium CarbonateHCID 2734328Dibenzofuran-4-boronic acidHCID 860610712-[(6-Chloro)pyrimidin-4-ylamino]-1-methyl-4-nitrobenzene2×

Produkt 1

HCID 66963353(6-Dibenzofuran-4-yl-pyrimidin-4-yl)-(2-methyl-5-nitro-phenyl)-amine

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

An aqueous Na2CO3-solution (11.0 g, 104 mmol carbonate in 104 mL of water) is stirred with (6-chloropyrimidin-4-yl)-(2-methyl-5-nitro-phenyl)-amine (compound C3) (2.80 g, 10.6 mmol), 4-dibenzofuranboronic acid (3.36 g, 15.9 mmol) and bistriphenylphosphinpalladiumdichloride (0.74 g, 1.1 mmol) in ethylenglycoledimethylether (168 mL). The mixture is heated to 80° C. After 1 h the mixture is cooled and filtered. The product is purified by flash silica gel chromatography.

Aufarbeitung

  1. temperatureAfter 1 h the mixture is cooled
  2. filtrationfiltered
  3. customThe product is purified by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c87edab8d59447bfb1cf8ea8b1c2d21a
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879853B2

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