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

HRID 1258228Notes

Reaction equation

HRID 1258228 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]

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 83717Copper iodideCatalystHCID 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-89d5616bbad54741beea848460d42c42
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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