3,3-Dianilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-2-propen-1-one → 2-anilino-7-chloro-6-fluoro-1-phenyl-1,8-naphthyridin-4(1H)-one

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Reaktionsgleichung

[NH:1]([C:8]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:9][C:10]([C:12]1[C:13](Cl)=[N:14][C:15]([Cl:19])=[C:16]([F:18])[CH:17]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>O1CCOCC1>[NH:1]([C:8]1[N:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:13]2[C:12]([C:10](=[O:11])[CH:9]=1)=[CH:17][C:16]([F:18])=[C:15]([Cl:19])[N:14]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 3,3-dianilino-1-(2,6-dichloro-5-fluoro-3-pyridinyl)-2-propen-1-one (2.3 g, 5.7 mmol) and t-BuOK (1.28 g, 11.4 mmol) in dioxane (80 mL) was stirred at 80° C. overnight. The reaction was cooled, concentrated in vacuo, diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. Silica gel flash chromatography of the residue provided 2-anilino-7-chloro-6-fluoro-1-phenyl-1,8-naphthyridin-4(1H)-one (1.0 g, 50%10) as a light yellow solid: LCMS RT: 2.60 min, MH+: 366.8. Tis transformation can be accomplished by using the combination of other aprotic solvents such as DMF, and THF with other bases such as NaH.

Aufarbeitung

temperatureThe reaction was cooled
concentrationconcentrated in vacuo
additiondiluted with water
extractionextracted with EtOAc
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-478e347ee69145e48014b8ce7a396b42
Quelldatensatz: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06900205B2

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