Water → Methyl 3-amino-6-chloro-2-methylisonicotinate

HRID 887704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887704
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6](Br)[C:5]=1[NH2:12].[C:14](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.O>O1CCOCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([CH3:14])[C:5]=1[NH2:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 59355453Methyl 3-amino-2-bromo-6-chloro-4-pyridinecarboxylate

Produkt 1

HCID 59355376Methyl 3-amino-6-chloro-2-methylisonicotinateAusbeute 26,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3-Amino-2-bromo-6-chloroisonicotinic acid methyl ester (500 mg), potassium carbonate (829 mg), tetrakis(triphenyl phosphine)palladium(0) and trimethylboroxine (276 mg) were suspended in dioxane (15 mL). Water (1.5 mL) was added and the mixture was degassed using subsequent evaporation and flushing with nitrogen (5×). The reaction mixture was stirred under reflux for 7 hours. After cooling to room temperature, the mixture was quenched with water and extracted 2× with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate=3:1, Rf=0.25) to afford 100 mg of the title compound of the formula

Aufarbeitung

  1. customthe mixture was degassed
  2. customevaporation
  3. customflushing with nitrogen (5×)
  4. temperatureunder reflux for 7 hours
  5. customthe mixture was quenched with water
  6. extractionextracted 2× with ethyl acetate
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuum
  10. customThe residue was purified by column chromatography (silica 60, hexane/ethyl acetate=3:1, Rf=0.25)

Quellen und Nachweise

ORD-Eintrag
ord-fdd725c27c344041857b94a3b8c3062d
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247431B2

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