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

HRID 570846
Notes
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Reaction equation

HRID 570846 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 37214604-Phenyl-1H-pyrrole-3-carbonitrileHCID 3847769Ethyl 2-bromoisonicotinate

Product 1

HCID 594778322-(3-Cyano-4-phenylpyrrole-1-yl)isonicotinic acid ethyl esterYield 35%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent

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

  1. customThe insoluble material was removed by filtration through Celite
  2. concentrationthis filtrate was concentrated
  3. 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-fea73fa641114481b0084c1ccb5dd478
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023882B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes