2-Methylpyridine → 3-[(7-Methoxynaphthalen-2-yl)oxy]pyridin-2-amine

HRID 2035790

Reaktionsgleichung

N1C=CC=CC=1C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][C:24]([OH:28])=[CH:25]2)=[CH:20][CH:19]=1.Br[C:30]1[C:31]([NH2:36])=[N:32][CH:33]=[CH:34][CH:35]=1>[Cu]I.O.CS(C)=O>[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][C:24]([O:28][C:30]3[C:31]([NH2:36])=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:25]2)=[CH:20][CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

A mixture of picoline acid (0.427 g), tripotassium phosphate (11.04 g), copper (I) iodide (0.660 g), 7-methoxynaphthalen-2-ol (6.04 g), 3-bromopyridin-2-amine (3 g) and DMSO (50 mL) was stirred under a nitrogen atmosphere at 140° C. overnight. Water was added, and the mixture was filtered through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and basic silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.667 g) as a pale-yellow solid.

Aufarbeitung

filtrationthe mixture was filtered through celite
extractionthe filtrate was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane) and basic silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag: ord-6daec4675cfa4e59b84d255a1033ab74
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08575154B2

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