O-Xylene → 8-Ethyl-7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one

HRID 656905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656905
[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13]CC=C)[CH:9]=[CH:8]2)[CH3:2].[C:18]1(C)[C:19](C)=CC=C[CH:23]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:19][CH:18]=[CH2:23])[C:10](=[O:13])[CH:9]=[CH:8]2)[CH3:2]

Komponenten

4

Edukt 2

HCID 7237O-XyleneHCID 689954698-Ethyl-7-fluoro-2-(2-propen-1-yloxy)-1,5-naphthyridine

Produkt 1

HCID 689929808-Ethyl-7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-oneAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

8-Ethyl-7-fluoro-2-(2-propen-1-yloxy)-1,5-naphthyridine (0.660 g, 2.84 mmol) was dissolved in xylene (14 ml) at rt under argon, whereupon tetrakis(triphenylphosphine)palladium (0.329 g, 0.284 mmol) was added. The reaction was then heated to 150° C. for 30 mins. Reaction was then cooled, a solid then precipitated out which was filtered. The filtrate was then purified by column chromatography on silica gel eluting with 0-100% EtOAc in hexane then 0-20% MeOH in EtOAc gradient to give title compound as a white solid (0.181 g, 27%).

Aufarbeitung

  1. additionwas added
  2. customReaction
  3. temperaturewas then cooled
  4. customa solid then precipitated out which
  5. filtrationwas filtered
  6. customThe filtrate was then purified by column chromatography on silica gel eluting with 0-100% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4b91c623732b4dd6bbe63d67594f45de
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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