Potassium Carbonate → HCID 68282777, Verbindung

HRID 624003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624003
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CCOC(C)=O>[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][CH2:14][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 5731291-(2-Bromoethyl)-3-fluorobenzene

Produkt 1

HCID 68282777HCID 68282777, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-nitro-1H-pyrazole (450 mg, 3.86 mmol) in acetone (15 mL), 3-fluorophenethyl bromide (784 mg, 3.86 mmol), K2CO3 (2.68 g, 19.301 mmol) and tetrabutylammonium bromide (120 mg, 0.38 mmol) was added. The white suspension was stirred at rt for 2 h, then the reaction mixture was diluted with H2O and EtOAc. The org. layer was separated and the aq. layer was extracted with EtOAc (1×). The combined org. layers were dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification of by FC (EtOAc/hept 3:7) gave 1-(3-fluorophenethyl)-4-nitro-1H-pyrazole as a off-white solid. LC-MS conditions B: tR=0.75 min, [M+H]+=no ionization.

Aufarbeitung

  1. customlayer was separated
  2. extractionthe aq. layer was extracted with EtOAc (1×)
  3. dry with materiallayers were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of by FC (EtOAc/hept 3:7)

Quellen und Nachweise

ORD-Eintrag
ord-04a2d683b06c49c390483f376b309d5e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303023B2

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