Pyridine → HCID 57749427, Verbindung

HRID 1162468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162468
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([NH2:10])[N:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:17]=1.N1C=CC=CC=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>CN(C1C=CN=CC=1)C.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([NH:10][C:24](=[O:26])[CH3:25])[N:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:17]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 57749423HCID 57749423, Verbindung

Produkt 1

HCID 57749427HCID 57749427, VerbindungAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a 250 mL round-bottomed flask was added 6-bromo-1-(pyridin-2-yl)-1H-benzo[d]imidazol-2-amine (1.00 g, 3.46 mmol), dichloromethane (35 mL), pyridine (0.419 mL, 5.19 mmol), acetic anhydride (0.343 mL, 3.63 mmol) and DMAP (0.0042 g, 0.035 mmol). The mixture was stirred at 25° C. for 2.5 days. The mixture was concentrated and taken up in MeOH/CH2Cl2 and then concentrated onto silica. Purification by silica gel chromatography (0.5 to 4.0% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a pink solid (0.673 g, 58%). MS (ESI, positive ion) m/z: 331 (M(79Br)+1).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. concentrationconcentrated onto silica
  3. customPurification by silica gel chromatography (0.5 to 4.0% MeOH (2 M in NH3)/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-1fece18a65424b63b5987e90fde425c7
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820665B2

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