2,2'-Bipyridine → HCID 57786250, Verbindung

HRID 1628683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628683
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[NH:11][CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1I.N1C=CC=CC=1C1C=CC=CN=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.[Cu]I>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:22]4[CH:21]=[CH:20][C:19]([Cl:18])=[CH:24][C:23]=4[Cl:25])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 14742,2'-BipyridineHCID 10796Cesium carbonateHCID 968642,4-Dichloro-1-iodobenzeneHCID 1363879919-Chloro-6-nitro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

Produkt 1

HCID 57786250HCID 57786250, VerbindungAusbeute 5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 9-chloro-6-nitro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (Reference Example 108; 10.0 g, 39.6 mmol), 2,4-dichloro-1-iodobenzene (54.0 g, 197.9 mmol), copper(I) iodide (7.57 g, 39.6 mmol), 2,2′-bipyridyl (12.3 g, 79.2 mmol) and cesium carbonate (25.8 g, 79.2 mmol) in N,N-dimethylformamide (600 mL) was stirred at 150° C. for 12 hr. The mixture was diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-25% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (750 mg, 1.88 mmol, 5%) as a light yellow amorphous.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel eluting with a 10-25% ethyl acetate/n-hexane gradient mixture
  5. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-75ee9bc8c9c6469a8843a3079c70b992
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

Notizen zur Reaktion

Wird geladen…