2-Chloro-5-fluoropyridine → 4-(5-Fluoro-2-pyridyl)-1-trityl-1H-imidazole

HRID 431984

Reaktionsgleichung

Reaktionsgleichung von HRID 431984
C([Sn](CCCC)(CCCC)[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)CCC.Cl[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][N:40]=1>C1(C)C=CC=CC=1>[F:45][C:42]1[CH:43]=[CH:44][C:39]([C:6]2[N:7]=[CH:8][N:9]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:10]=2)=[N:40][CH:41]=1

Komponenten

4

Edukt 2

HCID 27828012-Chloro-5-fluoropyridineHCID 118281174-(Tributylstannyl)-1-tritylimidazole

Produkt 1

HCID 219424474-(5-Fluoro-2-pyridyl)-1-trityl-1H-imidazoleAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To the solution of 4-Tributylstannyl-1-trityl-1H-imidazole (1.00 g, 1.67 mmol) in toluene (10 ml) added 2-Chloro-5-fluoropyridine (0.31 g, 2.38 mmol) and tetrakis(triphenylphoshine)palladium (0) (0.19 g, 0.17 mmol), sequentially. The resulting brownish yellow reaction mixture was heated at reflux under argon overnight. The reaction mixture was cooled to room temperature and concentrated in-vacuo. The residue was purified on silica gel using 30% diethyl ether in hexanes to isolate 4-(5-Fluoro-2-pyridyl)-1-trityl-1H-imidazole (0.23 g) as a clear oil.

Aufarbeitung

  1. temperatureThe resulting brownish yellow reaction mixture was heated
  2. temperatureat reflux under argon overnight
  3. concentrationconcentrated in-vacuo
  4. customThe residue was purified on silica gel using 30% diethyl ether in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ddcfbe05e74f4554b532bafb89cc1472
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660753B2

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