Potassium Carbonate → HCID 18472341, Verbindung

HRID 1277203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1277203
[CH3:1][N:2]([O:12][CH3:13])[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=1)=[O:4].B([O-])([O-])O[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]([O:12][CH3:13])[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:10]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 866453334-Methylphenyl borate

Produkt 1

HCID 18472341HCID 18472341, VerbindungAusbeute 102,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 66602552Toluene-ethanol waterLösungsmittel

Versuchsvorschrift

Under argon atmosphere, a solution of N-methyl-N-methoxy-5-bromopyridine-3-carboxamide (3.70 g), 4-methyl-phenyl borate (2.26 g) and potassium carbonate (4.17 g) in toluene-ethanol-water (100-10-10 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.52 g), and the mixture was refluxed for 16 hours and cooled to room temperature. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:2→1:1) to give N-methyl-N-methoxy-5-(4-methylphenyl)pyridine-3-carboxamide (3.97 g) as yellow oil.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 16 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1:2→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c397168a1d31463b85c383828ac35d8e
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166006

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