1-(3-Methylpyridin-2-yl)ethan-1-one → 5-Chloro-2-(3-methylpyridin-2-yl)-1,8-naphthyridine

HRID 1724876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724876
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[C:11]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)(=O)[CH3:12].CC([O-])(C)C.[K+]>C1COCC1>[Cl:10][C:6]1[CH:7]=[CH:8][N:9]=[C:2]2[C:3]=1[CH:4]=[CH:12][C:11]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)=[N:1]2

Komponenten

5

Edukt 3

HCID 130686691-(3-Methylpyridin-2-yl)ethan-1-oneHCID 23665647Potassium tert-butoxideHCID 462035412-Amino-4-chloropyridine-3-carbaldehyde

Produkt 1

HCID 575610685-Chloro-2-(3-methylpyridin-2-yl)-1,8-naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

Dissolve 2-amino-4-chloronicotinaldehyde (156 mg, 1.0 mmol) and 2-acetyl-3-methylpyridine (136 mg, 1.0 mmol) in anhydrous THF (5.0 mL) and cool it to −20° C. under N2 atmosphere. Add in portion t-BuOK (224 mg, 2.0 mmol) to the reaction mixture and stir the mixture at 110° C. for 2 hours. Concentrate the reaction mixture under vacuum, dilute the residue with water (10 mL), filter the solid, wash the solid with water and dry under high vacuum to afford the title product as a yellow colored solid.

Aufarbeitung

  1. concentrationConcentrate the reaction mixture under vacuum
  2. additiondilute the residue with water (10 mL)
  3. filtrationfilter the solid
  4. washwash the solid with water
  5. customdry under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-55a15a94dd2845c5881bd7d5b2d23bf3
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488740B2

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