Potassium Carbonate → 4-iodo-1-[(4-methoxyphenyl)methyl]-1H-pyrazole

HRID 38235

Reaktionsgleichung

Reaktionsgleichung von HRID 38235
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Cl[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 770224-Iodopyrazole

Produkt 1

HCID 574219364-iodo-1-[(4-methoxyphenyl)methyl]-1H-pyrazoleAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

According to Scheme 6 Step 1: A suspension of 4-iodo-1H-pyrazole (26.3 mmol, 5.11 g), 1-(chloromethyl)-4-methoxybenzene (29.0 mmol, 3.95 mL) and K2CO3 (39.5 mmol, 5.46 g) in acetonitrile (150 mL) was heated at 60° C. overnight. The reaction mixture was cooled to room temperature and was filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using DCM as eluent to afford 4-iodo-1-(4-methoxybenzyl)-1H-pyrazole (23.2 mmol, 7.3 g, 88%) as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-aefa367428334f35889df964d4cf7e2b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524718B2

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