Cesium carbonate → 6-Bromo-1-[(4-methoxyphenyl)methyl]-1H-imidazo[4,5-b]pyridine

HRID 1297328

Reaktionsgleichung

Reaktionsgleichung von HRID 1297328
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH:9]=[N:8][C:5]2=[N:6][CH:7]=1.Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=[N:8][C:5]2=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 9115786-Bromo-4H-imidazo[4,5-b]pyridine

Produkt 1

HCID 589145476-Bromo-1-[(4-methoxyphenyl)methyl]-1H-imidazo[4,5-b]pyridineAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-1H-imidazo[4,5-b]pyridine (500 mg, 2.52 mmol) and 1-chloromethyl-4-methoxy-benzene (394.6 mg, 2.52 mmol) in DMF (10 mL) was added Cs2CO3 (902 mg, 2.77 mmol). The reaction mixture was stirred at room temperature for 2 hours, and then partitioned between EtOAc and water. The organic layer was dried over MgSO4, and concentrated. The residue was purified on a silica gel column eluting with EtOAc-Hexane to provide 6-bromo-1-(4-methoxy-benzyl)-1H-imidazo[4,5-b]pyridine (450 mg).

Aufarbeitung

  1. custompartitioned between EtOAc and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column
  5. washeluting with EtOAc-Hexane

Quellen und Nachweise

ORD-Eintrag
ord-ee4bb69717474286a71ff8b0695a2bd4
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250417B2

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