Cesium carbonate → 2-Chloro-4-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyridine

HRID 2194384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194384
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[NH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:16][C:17]1[CH:22]=[C:21](F)[CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:16][C:17]1[CH:22]=[C:21]([N:13]2[CH:14]=[C:10]([C:9]#[C:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[N:11]=[C:12]2[CH3:15])[CH:20]=[CH:19][N:18]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27827922-Chloro-4-fluoropyridineHCID 178432693HCID 178432693, Verbindung

Produkt 1

HCID 866498792-Chloro-4-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyridineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 400 mg (1.85 mmol) of 4-(3-chloro-phenylethynyl)-2-methyl-1H-imidazole and 1.12 ml (1.46 g, 11.1 mmol) of 2-chloro-4-fluoropyridine in 5 ml of DMF were added 1.2 g (3.69 mmol) of cesium carbonate. The mixture was heated to 100° C. for 4 h, allowed to cool and concentrated in vaccuo. The residue was taken up in 20 ml ethyl acetate and the organic phase was washed twice with 20 ml of water and dried over magnesium sulfate. After treatment with charcoal, the solution was filtered and concentrated to yield 531 mg (1.62 mmol, 88%) of the title compound as an off-white crystalline solid, MS: m/e=328.1, 330.1 (M+H+).

Aufarbeitung

  1. temperatureto cool
  2. concentrationconcentrated in vaccuo
  3. washthe organic phase was washed twice with 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter treatment with charcoal, the solution was filtered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e845b2b862474653b7eb8a40a0d92c37
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334287B2

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