Pyridine, 4-(4,5-dimethyl-4H-1,2,4-triazol-3-yl)- → 4-(5-{2-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-yl]-propyl}-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridine

HRID 273166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 273166
[Li]CCCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[C:8]1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.Br[CH:20]([C:22]1[N:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[O:24][N:23]=1)[CH3:21]>C1COCC1>[Cl:33][C:29]1[CH:28]=[C:27]([C:25]2[O:24][N:23]=[C:22]([CH:20]([CH3:21])[CH2:12][C:11]3[N:7]([CH3:6])[C:8]([C:13]4[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=4)=[N:9][N:10]=3)[N:26]=2)[CH:32]=[CH:31][CH:30]=1

Komponenten

5

Edukt 3

HCID 11600754Pyridine, 4-(4,5-dimethyl-4H-1,2,4-triazol-3-yl)-HCID 578379313-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazoleHCID 178418339Butyllithium

Produkt 1

HCID 596673664-(5-{2-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-yl]-propyl}-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridineAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

84 microl (0.21 mmol, 2.5 M) n-BuLi was added dropwise to a solution of 37 mg (0.21 mmol) 4-(4,5-dimethyl-4H-[1,2,4]triazol-3-yl)-pyridine in 2.1 ml THF at 0° C. After 20 min a solution of 60 mg (0.21 mmol) 3-(1-bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazole was added dropwise. The reaction mixture was allowed to reach room temperature and stirred over night. NH4Cl(sat) was added and the mixture was extracted twice with EtOAc. The organic phase was dried and concentrated. Flashchromatography (CH2Cl2/MeOH 20:1) afforded 7.7 mg (10%) of the desired product. 1H NMR (CDCl3), d (ppm): 1.57 (d, 3 H) 3.16 (m, 1 H) 3.38 (m, 1 H) 3.71 (s, 3 H) 3.84 (d, 1 H) 7.46 (t, 1 H) 7.55 (m, 1 H) 7.58 (m, 2 H) 7.98 (m, 1 H) 8.10 (t, 1 H) 8.77 (d, 2 H)

Aufarbeitung

  1. customto reach room temperature
  2. extractionthe mixture was extracted twice with EtOAc
  3. customThe organic phase was dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-13dda66d8e6f454187b700922620fc93
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456200B2

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