Citric Acid → 2-(5-Methoxy-pyridin-2-yl)-benzoic acid diethylamide

HRID 541149

Reaktionsgleichung

Reaktionsgleichung von HRID 541149
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][N:11]=1.[CH2:18]([N:20]([CH2:32][CH3:33])[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O)=[O:22])[CH3:19].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH2:32]([N:20]([CH2:18][CH3:19])[C:21](=[O:22])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][N:11]=1)[CH3:33]

Komponenten

8

Edukt 4

HCID 311Citric AcidHCID 62657Potassium Phosphate, TribasicHCID 4190636(2-(Diethylcarbamoyl)phenyl)boronic acidHCID 151690002-Chloro-5-methoxypyridine

Produkt 1

HCID 594927872-(5-Methoxy-pyridin-2-yl)-benzoic acid diethylamideAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under an argon atmosphere, a mixture of tripotassium phosphate (6.24 g) and water (15 ml) was added to a mixture of 2-chloro-5-methoxy-pyridine (2.05 g), 2-(diethylcarbamoyl)benzeneboronic acid (4.65 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex (0.584 g) and toluene (30 ml), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled to room temperature, water (20 ml), citric acid (2.2 g) and ethyl acetate were added and the mixture was stirred and filtered through celite. The filtrate was partitioned in a separatory funnel. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/2) to give a roughly purified product (1.144 g) of the title compound. This product was directly used for the next reaction without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred
  3. filtrationfiltered through celite
  4. customThe filtrate was partitioned in a separatory funnel
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/2)

Quellen und Nachweise

ORD-Eintrag
ord-996e065bbc964b5c82d86c73e3dba0a9
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871934B2

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