Water → 2-(2-Fluorophenyl)-1,5-naphthyridine-3-carbonitrile

HRID 473405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473405
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][C:10]#[N:11].O1CCO[CH:14]1[C:18]1[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:10]#[N:11])=[CH:14][C:18]2[C:23](=[CH:22][CH:21]=[CH:20][N:19]=2)[N:24]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 3293632-(1,3-Dioxolanyl)-3-aminopyridineHCID 49627493-(2-Fluorophenyl)-3-oxopropanenitrile

Produkt 1

HCID 583186452-(2-Fluorophenyl)-1,5-naphthyridine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3-(2-Fluorophenyl)-3-oxopropanenitrile (1.5 g, 9.2 mmol) and 2-(1,3-dioxolan-2-yl)-3-pyridinamine (1.68 g, 10.12 mmol) were dissolved in toluene (100 mL). To the mixture was added catalytic amount of p-TSA (300 mg) and the reaction flask equipped with Dean-Stark assembly was heated for 4 h at 120° C. After completion of reaction, the reaction mixture was treated with water and ethyl acetate. The organic layer was separated and the aqueous layer was back extracted with ethyl acetate. The organic layers were combined and dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a thick oily mass. The oily mass was then purified by silica gel column chromatography using 20% of ethyl acetate and hexane as eluent to give 2-(2-fluorophenyl)-1,5-naphthyridine-3-carbonitrile: 1H-NMR (CDCl3) δ: 7.2-7.0 (m, 3H), 7.8-7.4 (m, 3H), 8.4 (d, 1H), 9.1 (s, 1H).

Aufarbeitung

  1. customthe reaction flask equipped with Dean-Stark
  2. customAfter completion of reaction
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was back extracted with ethyl acetate
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give a thick oily mass
  8. customThe oily mass was then purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dc508b87b49640be9367c8633f1e1292
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633313B2

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