HCID 90204301, Verbindung → HCID 90204051, Verbindung

HRID 1480187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1480187
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][C:3]=1[C:9]1([OH:13])[CH2:12][O:11][CH2:10]1.[C:14]([Zn]C#N)#[N:15]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].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]>[Cl:1][C:2]1[C:3]([C:9]2([OH:13])[CH2:12][O:11][CH2:10]2)=[CH:4][N:5]=[C:6]([C:14]#[N:15])[CH:7]=1

Komponenten

6

Edukt 2

HCID 90204301HCID 90204301, VerbindungHCID 178514179HCID 178514179, Verbindung

Produkt 1

HCID 90204051HCID 90204051, VerbindungAusbeute 155,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-(4,6-dichloropyridin-3-yl)oxetan-3-ol (example 123a, 5.0 g, 22.7 mmol) in dry DMF (100 ml) under argon atmosphere was added dicyanozinc (1.47 g, 12.5 mmol), DPPF (1.26 g, 2.27 mmol) and Pd2(dba)3 (1.04 g, 1.14 mmol). The reaction mixture was then stirred at 100° C. for two hours. DMF was removed in vacuo and the obtained residue was dissolved in ethyl acetate and poured into a separatory funnel. The organic phase was extracted with a saturated solution of ammonium chloride (colloids formed and were removed by filtration on a pad of celite). The organic phase was collected and the aqueous phase was back-extracted with ethyl acetate. Combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (4.1 gr, 86%); MS (ESI, m/z): 211.1 (M+H+).

Aufarbeitung

  1. customDMF was removed in vacuo
  2. dissolutionthe obtained residue was dissolved in ethyl acetate
  3. additionpoured into a separatory funnel
  4. extractionThe organic phase was extracted with a saturated solution of ammonium chloride (colloids
  5. customformed
  6. customwere removed by filtration on a pad of celite)
  7. customThe organic phase was collected
  8. extractionthe aqueous phase was back-extracted with ethyl acetate
  9. dry with materialCombined organic phases were dried over sodium sulfate
  10. customevaporated down to dryness
  11. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Quellen und Nachweise

ORD-Eintrag
ord-dcbddfcb1f354dcc8f0dc19bf45b5146
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409866B2

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