Ammonium Chloride → 2-Amino-6-(2-furyl)-5-(4-methoxy-3-pyridyl)-3-pyridinecarbonitrile

HRID 353224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353224
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:7](Br)=[CH:6][C:3]=1[C:4]#[N:5].[Cl-].[NH4+:17]>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:4]#[N:5])=[CH:6][C:7]([C:8]2[CH:7]=[N:17][CH:13]=[CH:14][C:10]=2[O:11][CH3:12])=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 129921342-Amino-5-bromo-6-(2-furyl)nicotinonitrile

Produkt 1

HCID 227079912-Amino-6-(2-furyl)-5-(4-methoxy-3-pyridyl)-3-pyridinecarbonitrileAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-amino-5-bromo-6-(2-furyl)nicotinonitrile (1.80 g, 6.82 mmol), 2-methoxy-5-(1,1,1-tributylstannyl)pyridine (5.20 g, 13.1 mmol) and dichlorobis(triphenylphosphine) palladium (II) (480 mg, 0.634 mmol) in N,N-dimethylformamide (18 ml) was stirred at 80° C. for 2 hours in a nitrogen atmosphere. After cooling as it was, the reaction solution was diluted with ethyl acetate and an aqueous saturated solution of ammonium chloride. The organic layer was washed with an aqueous saturated solution of ammonium chloride (×2), then dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=8:1, 4:1), and then suspended in diethyl ether. The resulting solid was collected by filtration and washed with diethyl ether, to give the title compound (1.12 g, 56%) as a yellow solid.

Aufarbeitung

  1. temperatureAfter cooling as it
  2. washThe organic layer was washed with an aqueous saturated solution of ammonium chloride (×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. washThe residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=8:1, 4:1)
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4562e47e2bd243ea824616e00c0b0e90
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750232B2

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