4-(2,2-dimethylbutyl)-2-methyl-1-trityl-1H-imidazole → 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

HRID 216394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216394
C([Li])CCC.[CH3:6][C:7]([CH3:36])([CH2:34][CH3:35])[CH2:8][C:9]1[N:10]=[C:11]([CH3:33])[N:12]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1.[F:37][C:38]1[CH:39]=[CH:40][C:41]([C:44]2[CH:55]=[CH:54][C:47]([C:48](N(OC)C)=[O:49])=[CH:46][CH:45]=2)=[N:42][CH:43]=1>O1CCCC1>[CH3:6][C:7]([CH3:36])([CH2:34][CH3:35])[CH2:8][C:9]1[N:10]=[C:11]([CH2:33][C:48]([C:47]2[CH:46]=[CH:45][C:44]([C:41]3[CH:40]=[CH:39][C:38]([F:37])=[CH:43][N:42]=3)=[CH:55][CH:54]=2)=[O:49])[N:12]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1

Komponenten

5

Edukt 3

HCID 591619684-(2,2-dimethylbutyl)-2-methyl-1-trityl-1H-imidazoleHCID 866384894-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Produkt 1

HCID 686681262-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-Butyllithium (2.5 M in hexanes) (0.53 mL, 1.32 mmol) was added to a solution of 4-(2,2-dimethylbutyl)-2-methyl-1-trityl-1H-imidazole (360 mg, 0.88 mmol) in tetrahydrofuran (15 mL) at −78° C. dropwise. After stirring at −78° C. for 40 min, 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide (340 mg, 1.32 mmol) in tetrahydrofuran (5 mL) was added dropwise. After warming slowly to ambient temperature, the reaction mixture was quenched with saturated aqueous ammonium chloride. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-20% ethyl acetate/hexane afforded 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone contaminated with an unidentified byproduct. This material was used in the next step without further purification.

Aufarbeitung

  1. temperatureAfter warming slowly to ambient temperature
  2. customthe reaction mixture was quenched with saturated aqueous ammonium chloride
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-96d46e947a1c423bbd0e6f2aaff59578
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193228B2

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