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

HRID 2039826

Reaction equation

[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

Participants

Conditions

Temperature: 130 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-e243633102c74b388dd3499f3436c046
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580813B2

Linked notes

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