Dimethylformamide → 4-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine-2-carbonitrile

HRID 1959600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959600
Cl[C:2]1[C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:6]([Cl:16])[CH:5]=[CH:4][N:3]=1.[CH3:17][N:18](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.[Zn].C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:16][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:17]#[N:18])[C:7]=1[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1

Komponenten

8

Edukt 2

HCID 6228DimethylformamideHCID 86645362HCID 86645362, Verbindung

Produkt 1

HCID 670775644-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 11192Zinc AcetateKatalysatorHCID 23994ZincKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

2,4-Dichloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine (455 mg. 1.74 mmol) was dissolved in a mixture of DMF (3 mL) and water (30 μL). The following reagents were added subsequently: zinc cyanide (112 mg. 0.95 mmol), zinc dust (9.1 mg. 139 μmol), zinc acetate (25.5 mg. 139 μmol). 1,1′-bis(diphenylphosphino)ferrocene (58 mg. 104 μmol) and tris(dibenzylideneacetone)palladium (0). The reaction mixture was degassed two times and afterwards heated at 95° C. for 4 h. The solvents were removed in vacuo and the residue was pardoned between water (20 mL) and EtOAc (20 mL) and extracted with EtOAc (3×20 ml). The combined organic layers were washed with brine and dried over Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with hexane/EtOAc 10:1→5:1) to give the title compound. MS (m/z): 253.0 [M+H+].

Aufarbeitung

  1. additionThe following reagents were added subsequently
  2. customThe reaction mixture was degassed two times
  3. customThe solvents were removed in vacuo
  4. extractionextracted with EtOAc (3×20 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel (elution with hexane/EtOAc 10:1→5:1)

Quellen und Nachweise

ORD-Eintrag
ord-7cb16a4656344b03b88ce7122d259da3
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410134B2

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