Potassium Carbonate → 5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxybenzaldehyde

HRID 1473907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473907
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].Cl.Cl[CH2:14][C:15]1[C:16]([C:21]2[N:25]([CH:26]([CH3:28])[CH3:27])[N:24]=[CH:23][CH:22]=2)=[N:17][CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:26]([N:25]1[C:21]([C:16]2[C:15]([CH2:14][O:1][C:2]3[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=3)[CH:7]=[O:8])=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:22][CH:23]=[N:24]1)([CH3:28])[CH3:27]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 3583415-Hydroxy-2-MethoxybenzaldehydeHCID 86690720Pyridine, 3-(chloromethyl)-2-(1-(1-methylethyl)-1H-pyrazol-5-yl)-, hydrochloride (1:2)

Produkt 1

HCID 866907225-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxybenzaldehydeAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 5-hydroxy-2-methoxybenzaldehyde (395 mg, 2.58 mmol, 1 eq.), 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride (700 mg, 2.58 mmol, 1 eq.), and K2CO3 (1.4 g, 10.32 mmol, 4 eq.) in DMF (10.0 mL) was heated at 70° C. for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxybenzaldehyde (590 mg, 65%) as an off-white solid.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified on silica gel using
  5. additiona mixture of EtOAc and hexanes as eluent

Quellen und Nachweise

ORD-Eintrag
ord-3a3b3cb57aa845bf9a68673471a62647
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018210B2

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