Acetamide → N-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)acetamide

HRID 1049234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1049234
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:16])=[N:11][C:12](I)=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:17]([NH2:20])(=[O:19])[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>O1CCOCC1.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].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:20][C:17](=[O:19])[CH3:18])=[N:11][C:10]=2[CH3:16])[CH:5]=[CH:4][N:3]=1

Komponenten

8

Edukt 4

HCID 178AcetamideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 90403315HCID 90403315, Verbindung

Produkt 1

HCID 90402585N-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)acetamideAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
83 °C

Versuchsvorschrift

A solution of 3-((2-chloropyridin-4-yl)oxy)-6-iodo-2-methylpyridine (8.5 g, 24.53 mmol) in dioxane (100 mL) was sparged with argon, treated with acetamide (5.07 g, 86 mmol), Cs2CO3 (11.99 g, 36.8 mmol), X-Phos (0.585 g, 1.226 mmol) and Pd2(dba)3 (1.123 g, 1.226 mmol) and heated at 83° C. for 16 h. The mixture was cooled to RT, treated with EtOAc, solids removed via filtration through diatomaceous earth, rinsed well with EtOAc, and the filtrate washed with H2O, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)acetamide (3.8 g, 56%) as an off-white solid. MS (ESI) m/z: 278.0 (M+H+).

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. customremoved via filtration through diatomaceous earth
  3. washrinsed well with EtOAc
  4. washthe filtrate washed with H2O
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-7a540c3b0beb419386e69361b2edb6ea
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382228B2

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