Potassium Carbonate → 6-(1-Chloroisoquinolin-4-yloxy)nicotinonitrile

HRID 2060855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060855
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][N:3]=1.Cl[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 42818821-Chloro-4-hydroxyisoquinolineHCID 51520946-Chloro-3-pyridinecarbonitrile

Produkt 1

HCID 594013876-(1-Chloroisoquinolin-4-yloxy)nicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 1-chloro-4-hydroxyisoquinoline (1.0 g, 5.6 mmol) in DMF (16 mL), was added 6-chloronicotinonitrile (0.55 g, 4.0 mmol) and K2CO3 (1.65 g, 11.9 mmol). The reaction mixture was heated at 70° C. for 6.5 h. Solvent was removed in vacuo and residue partitioned between EtOAc (100 mL), THF (100 mL) and water (60 mL). The organic phase was washed with water (2×60 mL), 1M NaOH (2×40 mL), brine (40 mL) and dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=3.66 min; m/z (ES+)=282.0 [M+H]+.

Aufarbeitung

  1. customSolvent was removed in vacuo and residue
  2. custompartitioned between EtOAc (100 mL), THF (100 mL) and water (60 mL)
  3. washThe organic phase was washed with water (2×60 mL), 1M NaOH (2×40 mL), brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3c4ff8d0135045eaab7945089e091a7a
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278442B2

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