Water → 4-(3-Butyl-4-cyano-2-methylpyrrole-1-yl)benzoic acid ethyl ester

HRID 1516581Notes

Reaction equation

[CH2:1]([C:5]1[C:6]([C:11]#[N:12])=[CH:7][NH:8][C:9]=1[CH3:10])[CH2:2][CH2:3][CH3:4].[CH2:13]([O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=1)[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:13]([O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([N:8]2[CH:7]=[C:6]([C:11]#[N:12])[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:9]2[CH3:10])=[CH:19][CH:18]=1)[CH3:14]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 4-butyl-5-methyl-1H-pyrrole-3-carbonitrile (0.081 g), 4-fluoro-benzoic acid ethyl ester (0.10 g) and cesium carbonate (0.21 g) in N,N-dimethylformamide (3 mL) was stirred at 70° C. overnight. This reaction mixture was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/6) to give the title compound (0.032 g).

Workup

extractionthis mixture was extracted with ethyl acetate
washThis organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/6)

Sources & evidence

ORD record: ord-4fc2d61d6bce447a804432e37bc562e8
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227500B2

Reaction notes

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