2-[4-(1,3,4-Oxadiazol-2-yl)phenyl]acetonitrile → 3-(2-Fluoro-4-trifluoromethyl-phenyl)-5-(4-[1,3,4]oxadiazol-2-yl-phenyl)-3H-[1,2,3]triazol-4-ylamine

HRID 1639688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639688
C[O-].[Na+].[O:4]1[CH:8]=[N:7][N:6]=[C:5]1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=1.[N:18]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[F:31])=[N+:19]=[N-:20]>CO>[F:31][C:22]1[CH:23]=[C:24]([C:27]([F:29])([F:30])[F:28])[CH:25]=[CH:26][C:21]=1[N:18]1[C:16]([NH2:17])=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([C:5]3[O:4][CH:8]=[N:7][N:6]=3)=[CH:10][CH:11]=2)[N:20]=[N:19]1

Komponenten

5

Edukt 3

HCID 27395922-[4-(1,3,4-Oxadiazol-2-yl)phenyl]acetonitrileHCID 10942334Sodium MethoxideHCID 866450681-Azido-2-fluoro-4-(trifluoromethyl)benzene

Produkt 1

HCID 252156723-(2-Fluoro-4-trifluoromethyl-phenyl)-5-(4-[1,3,4]oxadiazol-2-yl-phenyl)-3H-[1,2,3]triazol-4-ylamineAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred and ice-cooled solution of sodium methoxide (0.158 g, 2.9252 mmol) in methanol (25 ml), commercial 2-[4-(1,3,4-oxadiazol-2-yl)phenyl]acetonitrile (0.430 g, 2.3401 mmol) and 1-azido-2-fluoro-4-trifluoromethyl-benzene (0.400 g, 1.9501 mmol) are added under a nitrogen atmosphere. The reaction mixture is kept at 0° C. for 1 h, and then allowed to attain spontaneously room temperature overnight. The reaction mixture is concentrated, added water (30 ml), and extracted with ethylacetate (3×100 ml). The combined organic layers are dried over MgSO4, filtered and evaporated, to afford a pink solid (0.74 g, 97% mass balance). The crude residue is purified by column chromatography over silica gel (230-400 mesh), eluting with 50% ethylacetate in petroleum ether, to obtain the title compound as a yellow solid (0.280 g, 37% yield). M.p. 184.6-186.1° C. LC-ESI-HRMS of [M+H]+ shows 391.0927 Da. Calc. 391.093046 Da, dev. −0.9 ppm.

Aufarbeitung

  1. additionare added under a nitrogen atmosphere
  2. waitto attain spontaneously room temperature overnight
  3. concentrationThe reaction mixture is concentrated
  4. additionadded water (30 ml)
  5. extractionextracted with ethylacetate (3×100 ml)
  6. dry with materialThe combined organic layers are dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto afford a pink solid (0.74 g, 97% mass balance)
  10. customThe crude residue is purified by column chromatography over silica gel (230-400 mesh)
  11. washeluting with 50% ethylacetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-6e8acca2130f4c51a0bad3575fc65845
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110588B2

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