Picolinic acid → 3-(4-(3-Ethylphenoxy)phenyl)pyridin-2-amine

HRID 1622723

Reaktionsgleichung

N1C=CC=CC=1C(O)=O.[NH2:10][C:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:15][CH:14]=[CH:13][N:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH3:40])[CH:34]=1>[Cu]I.CS(C)=O>[CH2:39]([C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[O:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]2[C:11]([NH2:10])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:18][CH:19]=1)[CH3:40]

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

Copper(I) iodide (102 mg) was added to a mixture of picolinic acid (66.1 mg), 4-(2-aminopyridin-3-yl)phenol (500 mg), tripotassium phosphate (1710 mg), 1-bromo-3-ethylbenzene (596 mg) and DMSO (8 ml). The mixture was stirred at 130° C. under nitrogen for 4 hr. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc). Water and EtOAc were added and the extracted organic layer was washed with brine. Silica-gel was added to the organic layer and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane) to give the title compound (312.5 mg) as a pale yellow crystalline solid.

Aufarbeitung

additionActivated carbon was added
customthe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
additionWater and EtOAc were added
washthe extracted organic layer was washed with brine
additionSilica-gel was added to the organic layer
customthe volatiles were removed in vacuo
customwas purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-a616f52243f6401387f1fdc88e3803f5
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08778934B2

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