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

HRID 73373
Notes
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Reaction equation

HRID 73373 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[CH:2]1.[CH2:12]([O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][N:19]=[C:18](Br)[CH:17]=1)[CH3:13].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu](I)I.C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15](=[O:23])[C:16]1[CH:17]=[CH:18][N:19]=[C:20]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]#[N:11])=[CH:2]2)[CH:21]=1)[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2302823-CyanoindoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 3847769Ethyl 2-bromoisonicotinate

Product 1

HCID 584373112-(3-Cyanoindol-1-yl)isonicotinic acid ethyl esterYield 30.1%

Reagents, catalysts & solvents 2

HCID 83717
Copper iodide
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1H-indole-3-carbonitrile (0.1 g), 2-bromoisonicotinic acid ethyl ester (0.16 g), potassium phosphate (0.27 g), (1R,2R)-(−)-N,N′-dimethylcyclohexane-1,2-diamine (0.017 g), copper iodide (0.006 g) and toluene (0.7 mL) was stirred at 110° C. for 38 hours. The insoluble material was removed by filtration, and this filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90 to 66/34) to give the title compound (0.061 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthis filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90 to 66/34)

Sources & evidence

ORD record
ord-953e4f3bddfc4af7bead9475e160251d
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829040B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes