Potassium Phosphate, Tribasic → 2-(3-Cyano-4-phenylpyrrole-1-yl)isonicotinic acid ethyl ester

HRID 1516593Notes

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:25])[C:18]1[CH:23]=[CH:22][N:21]=[C:20](Br)[CH:19]=1)[CH3:15].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>C1(C)C=CC=CC=1.[Cu](I)I>[CH2:14]([O:16][C:17](=[O:25])[C:18]1[CH:19]=[CH:20][N:21]=[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:23]=1)[CH3:15]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 4-phenyl-1H-pyrrole-3-carbonitrile (0.1 g) in toluene (0.70 mL) were added 2-bromo-isonicotinic acid ethyl ester (0.19 g), potassium phosphate (0.31 g), (1R,2R)-(−)—N,N′-dimethylcyclohexane-1,2-diamine (0.02 g) and copper iodide (0.007 g) at room temperature, and this mixture was stirred at 110° C. for 24 hours. The insoluble material was removed by filtration through Celite, 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 (0.066 g).

Workup

customThe insoluble material was removed by filtration through Celite
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-1f592b469abe45179af6c2d684686c14
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227500B2

Reaction notes

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