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Ethyl Acetate → 3-(3-Cyanoindol-1-yl)benzoic acid ethyl ester

HRID 73372
Notes
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Reaction equation

HRID 73372 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][CH:19]=[C:18](I)[CH:17]=1)[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CS(C)=O.[Cu](I)I>[CH2:12]([O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([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:17]=1)[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 143542Ethyl 3-iodobenzoateHCID 2302823-Cyanoindole

Product 1

HCID 584374173-(3-Cyanoindol-1-yl)benzoic acid ethyl esterYield 66.5%

Reagents, catalysts & solvents 2

HCID 83717
Copper iodide
Catalyst
HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1H-indole-3-carbonitrile (0.28 g) in dimethyl sulfoxide (3 mL) were added 3-iodobenzoic acid ethyl ester (0.61 g), cesium carbonate (0.65 g), copper iodide (0.038 g) and N,N-dimethyl grycine (0.041 g), this mixture was stirred at 75° C. for 3 days. To this reaction mixture was added ethyl acetate, the insoluble material was removed by filtration and this filtrate was concentrated under reduced pressure. To this residue was added water, the precipitated solid was collected by filtration, and washed with water and n-hexane, and dried under reduced pressure at 40° C. to give the title compound (0.38 g).

Workup

  1. customthe insoluble material was removed by filtration
  2. concentrationthis filtrate was concentrated under reduced pressure
  3. additionTo this residue was added water
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water and n-hexane
  6. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-61e47699cfcb4f298d9b227daeab03f2
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