Potassium Carbonate → 5-Methoxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine

HRID 2039826

Reaktionsgleichung

[CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][NH:11][C:6]2=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>CS(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Cu]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:9]=[CH:10][N:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]2=[CH:7][N:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

To a mixture of 5-methoxy-1H-pyrrolo[2,3-c]pyridine (6.00 g, 40.5 mmol; cf. D. Mazéas et al., Heterocycles 50 (1999), 1065), copper(II) acetylacetonate (1.06 g, 4.05 mmol) and potassium carbonate (11.2 g, 81.0 mmol) in DMSO (63 ml) was added iodobenzene (4.99 ml, 44.6 mmol). The reaction mixture was stirred at 130° C. for 10 h. The mixture was then cooled to room temperature, and a solution of ammonium chloride (20% in water) was added. The mixture was filtered through celite and the filtrate extracted three times with EA. The organic layers were combined, dried over sodium sulfate, filtered and evaporated under reduced pressure. Column chromatography of the residue on silica gel (EA/HEP) gave 8.43 g of the title compound.

Aufarbeitung

temperatureThe mixture was then cooled to room temperature
filtrationThe mixture was filtered through celite
extractionthe filtrate extracted three times with EA
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-e243633102c74b388dd3499f3436c046
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08580813B2

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