2-Cyclohexen-1-one → ethyl 3-(3-oxocyclohexyl)-1H-indole-2-carboxylate

HRID 533251Notes

Reaction equation

HRID 533251 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[C:15]1(=[O:21])[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]1.FC(F)(F)S([O-])(=O)=O.[Bi+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C>[O:21]=[C:15]1[CH2:20][CH2:19][CH2:18][CH:17]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:16]1

Participants

5

Reactant 3

HCID 135942-Cyclohexen-1-oneHCID 73125Ethyl indole-2-carboxylateHCID 9917655Bi(OTf)3

Product 1

HCID 67316060ethyl 3-(3-oxocyclohexyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl 1H-indole-2-carboxylate (2.953 g) and cyclohex-2-enone (1.004 mL) were added to acetonitrile (50 mL). Bismuth (III) trifluoromethanesulfonate (341 mg) was added, and the solution was heated at 65° C. for two days. The solution was cooled, concentrated, and purified by flash column chromatography on silica gel with 10% increasing to 20% ethyl acetate in hexanes to provide the title compound.

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated
  3. custompurified by flash column chromatography on silica gel with 10%
  4. temperatureincreasing to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a52a3c7e7b014a8cb21fba3f9ae58f16
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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