2-Aminopyridine → Methyl 2-(2-pyridylamino)isonicotinate

HRID 452633

Reaktionsgleichung

Reaktionsgleichung von HRID 452633
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:12][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Komponenten

8

Edukt 3

HCID 104392-AminopyridineHCID 62657Potassium Phosphate, TribasicHCID 2736842Methyl 2-chloropyridine-4-carboxylate

Produkt 1

HCID 68664232Methyl 2-(2-pyridylamino)isonicotinateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of methyl 2-chloroisonicotinate (1.00 g, 5.83 mmol), 2-aminopyridine (658 mg, 6.99 mmol), tris(dibenzylideneacetone)dipalladium(0) (107 mg, 0.17 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (139 mg, 0.29 mmol) and tripotassium phosphate (3.09 g, 14.6 mmol) in toluene (30 mL) was heated under reflux under an argon atmosphere overnight. After cooling, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=9/1-2/3) and recrystallized from hexane/ethyl acetate to give the title compound (866 mg, yield 65%) as colorless crystals.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux under an argon atmosphere overnight
  3. temperatureAfter cooling
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=9/1-2/3)
  8. customrecrystallized from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5947a725ed7340a889cf8a5963cb710d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492378B2

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