Cesium carbonate → 3-chloro-5-({5-chloro-1-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]-1H-1,2,3-benzotriazol-4-yl}oxy)benzonitrile

HRID 505558

Reaktionsgleichung

Reaktionsgleichung von HRID 505558
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]3[N:18]=[N:17][NH:16][C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:28][C:29]1[O:30][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:32][N:33]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]3[N:18]=[N:17][N:16]([CH2:28][C:29]4[O:30][C:31]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)=[N:32][N:33]=4)[C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 3149412-(Chloromethyl)-5-phenyl-1,3,4-oxadiazoleHCID 178509930HCID 178509930, Verbindung

Produkt 1

HCID 684276303-chloro-5-({5-chloro-1-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]-1H-1,2,3-benzotriazol-4-yl}oxy)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (100 mg, 0.328 mmol), cesium carbonate (107 mg, 0.328 mmol) and 2-(chloromethyl)-5-phenyl-1,3,4-oxadiazole (64 mg, 0.328 mmol) were combined and suspended in DMF (2 mL). After 16 hours at room temperature, the reaction mixture was quenched with saturated aqueous ammonium chloride (1 mL) and extracted with EtOAc (2×25 mL). The combined organic fractions were evaporated under reduced pressure, and the resulting residue was purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. The product fractions were concentrated to yield the title compound. 1H NMR (DMSO-d6) δ 8.01 (d, J=8.9 Hz, 1H), 7.96 (d, J=8.3 Hz, 2H), 7.88 (d, J=8.9 Hz, 1H), 7.83 (m, 1H), 7.61 (m, 5H), 6.54 (s, 2H). HRMS (M+1)=463.0465.

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride (1 mL)
  2. extractionextracted with EtOAc (2×25 mL)
  3. customThe combined organic fractions were evaporated under reduced pressure
  4. customthe resulting residue was purified by reverse phase chromatography
  5. washeluting with 30-95% MeCN/H2O+0.1% TFA
  6. concentrationThe product fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7f41014884d44382a947c3cfeeb5303e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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