Cesium carbonate → tert-Butyl[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetate

HRID 505540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505540
[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+].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C=O)C>[C:32]([O:31][C:29](=[O:30])[CH2:28][N:16]1[C:15]2[CH:14]=[CH:13][C:12]([Cl:20])=[C:11]([O:10][C:8]3[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=3)[C:19]=2[N:18]=[N:17]1)([CH3:35])([CH3:34])[CH3:33]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 178509930HCID 178509930, Verbindung

Produkt 1

HCID 86624476tert-Butyl[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (500 mg, 1.64 mmol) and cesium carbonate (534 mg, 1.64 mmol) were suspended in DMF (5 mL) under N2. To this was added tert-butyl bromoacetate (336 mg, 1.72 mmol) After 1 hour, the reaction was quenched with saturated aqueous ammonium chloride (5 mL), diluted with water and the mixture extracted with ethyl acetate (2×25 mL). The combined organic fractions were washed with water (3×25 mL) and dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by automated column chromatography on silica gel (40 g) eluting with 0-15% EtOAc/hexanes to give the title product. LRMS (M+1)=418.9.

Aufarbeitung

  1. customthe reaction was quenched with saturated aqueous ammonium chloride (5 mL)
  2. additiondiluted with water
  3. extractionthe mixture extracted with ethyl acetate (2×25 mL)
  4. washThe combined organic fractions were washed with water (3×25 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by automated column chromatography on silica gel (40 g)
  9. washeluting with 0-15% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4fbce000015b4b79a3eb5e234ee4265d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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