Cesium carbonate → 4-(3-methyl-5-nitrophenyl)-1-(2-methylallyl)-1H-pyrazole

HRID 595159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595159
Br[CH2:2][C:3]([CH3:5])=[CH2:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:12][C:13]1[CH:14]=[C:15]([C:22]2[CH:23]=[N:24][NH:25][CH:26]=2)[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1>CC(N(C)C)=O>[CH3:12][C:13]1[CH:14]=[C:15]([C:22]2[CH:26]=[N:25][N:24]([CH2:4][C:3]([CH3:5])=[CH2:2])[CH:23]=2)[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 3577853-Bromo-2-methyl-1-propeneHCID 916191664-(3-methyl-5-nitrophenyl)-1H-pyrazole

Produkt 1

HCID 1182085014-(3-methyl-5-nitrophenyl)-1-(2-methylallyl)-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

3-Bromo-2-methylprop-1-ene (4.19 g, 31.0 mmol) and cesium carbonate (13.5 g, 41.3 mmol) were added to a solution of 4-(3-methyl-5-nitrophenyl)-1H-pyrazole (4.20 g, 20.7 mmol) in dimethylacetamide (41 mL) and stirred at 70° C. for 18 h. The mixture was allowed to cool to room temperature, passed through CELITE, washed with methanol, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane) to afford 4-(3-methyl-5-nitrophenyl)-1-(2-methylallyl)-1H-pyrazole. MS ESI calc'd. for C14H16N3O2 [M+H]+ 258. found 258.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washwashed with methanol
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-84596afe64144a46aed622af34e3e185
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242984B2

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