Cesium carbonate → 5-(3-Cyano-4-phenylpyrrole-1-yl)-2-methoxymethoxy-benzoic acid ethyl ester

HRID 570847Notes

Reaction equation

[C:1]1([C:7]2[C:8]([C:12]#[N:13])=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([O:16][C:17](=[O:29])[C:18]1[CH:23]=[C:22](Br)[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][O:27][CH3:28])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu](I)I.CS(C)=O>[CH2:14]([O:16][C:17](=[O:29])[C:18]1[CH:23]=[C:22]([N:10]2[CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]([C:12]#[N:13])=[CH:9]2)[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][O:27][CH3:28])[CH3:15]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 4-phenyl-1H-pyrrole-3-carbonitrile (0.2 g), 5-bromo-2-methoxymethoxy-benzoic acid ethyl ester (0.36 g), copper iodide (0.023 g), N,N-dimethylgrycine (0.025 g), cesium carbonate (0.39 g) and dimethylsulfoxide (3 mL) was stirred at 75° C. for 12 hours. After cooling to ambient temperature, the insoluble material was removed by filtration through Celite pad, and this filtrate was concentrated. This obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-66/34) to give the title compound (0.27 g).

Workup

temperatureAfter cooling to ambient temperature
customthe insoluble material was removed by filtration through Celite pad
concentrationthis filtrate was concentrated
customThis obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-66/34)

Sources & evidence

ORD record: ord-f1c7bbccf296464e94ceb25e50dbcd39
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023882B2

Reaction notes

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