Cesium carbonate → HCID 178491480, Verbindung

HRID 1696866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696866
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[C:12]([CH3:13])=[N:11][NH:10][C:9]=2[OH:14])[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:22]([CH3:34])[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[CH3:33])=[O:24]>CN(C=O)C>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[C:12]([CH3:13])=[N:11][NH:10][C:9]=2[O:14][CH:22]([CH3:34])[C:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=2[CH3:33])=[O:24])[N:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 189677762-Bromo-1-(4-methoxy-2-methyl-phenyl)-propan-1-one2×HCID 178432945HCID 178432945, Verbindung2×

Produkt 1

HCID 178491480HCID 178491480, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirring solution of 4-(3,5-dimethyl-[1,2,4]triazol-1-yl)-5-methyl-2H-pyrazol-3-ol (1 g, 5.18 mmol) (Intermediate A) in DMF (25 ml) was added Cs2CO3 (1.771 g, 5.43 mmol). The mixture was left to stir at 50° C. for 30 minutes and then treated with of 2-bromo-1-(4-methoxy-2-methyl-phenyl)-propan-1-one (Intermediate B) (1.397 g, 5.43 mmol) in DMF (10 ml). The mixture was stirred at 50° C. for 1 hour and concentrated in vacuo. The residue was dissolved in water (300 ml) and extracted with EtOAc (3×150 ml). The combined organic extracts were washed with NaHCO3, water, dried (MgSO4) and concentrated in vacuo to yield a pale yellow solid. Purification of the solid by chromatography on silica eluting with 20-100% EtOAc in iso-hexane afforded the title compound as a white solid; LC-MS Rt 1.03 mins; MS m/z 370.3 [M+H]+; Method 2minLC—30_v002.

Aufarbeitung

  1. waitThe mixture was left
  2. stirringThe mixture was stirred at 50° C. for 1 hour
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in water (300 ml)
  5. extractionextracted with EtOAc (3×150 ml)
  6. washThe combined organic extracts were washed with NaHCO3, water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto yield a pale yellow solid
  10. customPurification of the solid by chromatography on silica eluting with 20-100% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-17f3c51fae614adf86c3fcf9954dcf67
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163785B2

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