8-Hydroxyquinoline → Benzyl 4-(1-(4-(methylthio)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

HRID 1676189

Reaktionsgleichung

[O:1]=[C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:4][NH:3]1.Br[C:26]1[CH:31]=[CH:30][C:29]([S:32][CH3:33])=[CH:28][CH:27]=1.N1C2C(=CC=CC=2O)C=CC=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O.[Cu]I>[CH3:33][S:32][C:29]1[CH:30]=[CH:31][C:26]([N:3]2[CH:4]=[CH:5][C:6]([O:8][CH:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[O:16])[CH2:11][CH2:10]3)=[CH:7][C:2]2=[O:1])=[CH:27][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: 145 °C

Versuchsvorschrift

A mixture of benzyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (697 mg, 2.12 mmol), (4-bromophenyl)(methyl)sulfane (431 mg, 2.12 mmol, Aldrich), quinolin-8-ol (61.6 mg, 0.425 mmol, Alfa Aesar), potassium carbonate (381 mg, 2.76 mmol, EMD), Copper(I) iodide (81 mg, 0.43 mmol, Alfa Aesar) in DMSO (6 mL) was stirred at 145° C. overnight under Argon. The resulting mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to a green solid. The solid was purified by flash chromatography (SiO2, 0 to 5% MeOH in CH2Cl2) to yield 911 mg of desired product as a light green solid. MS (ESI) 451 (M+H).

Aufarbeitung

extractionextracted with EtOAc (2×)
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo to a green solid
customThe solid was purified by flash chromatography (SiO2, 0 to 5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag: ord-6d9fc287bb7647da962c5755fef186ed
Quelldatensatz: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08003796B2

Verknüpfte Notizen

Wird geladen…