Potassium Carbonate → 2-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine

HRID 626516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626516
F[C:2]1[C:3]([CH3:11])=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[OH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:19][C:15]1[CH:14]=[C:13]([O:12][C:2]2[C:3]([CH3:11])=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=2)[CH:18]=[CH:17][N:16]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 591847405-Fluoro-4-methyl-2-nitropyridineHCID 178516507HCID 178516507, Verbindung

Produkt 1

HCID 866416892-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridineAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-fluoro-4-methyl-2-nitropyridine (0.8 g, 5.12 mmol), 4-hydroxy-2-chloropyridine (0.996 g, 7.69 mmol) and K2CO3 (0.708 g, 5.12 mmol) in DMF (10 mL) was heated at 80° C. for 4 h. The mixture was cooled to RT, poured onto water, extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 5-((2-chloropyridin-4-yl)oxy)-4-methyl-2-nitropyridine (850 mg, 62%) as an off-white solid. MS (ESI) m/z: 266.0 (M+H+).

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. additionpoured onto water
  3. extractionextracted with EtOAc (2×)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-fdf4fb60fcbe4145ab6503576c355e6a
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309224B2

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