Benzyl Chloride → Ethyl 1-benzyl-5-chloro-1H-indole-2-carboxylate

HRID 902867Notes

Reaction equation

HRID 902867 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 78518Ethyl 5-chloroindole-2-carboxylate

Product 1

HCID 13295699Ethyl 1-benzyl-5-chloro-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-chloroindole-2-carboxylate (1.4 g) was dissolved in N,N-dimethylformamide (30 ml), and potassium carbonate (2.9 g) and benzyl chloride (2.4 ml) were added. The mixture was heated and stirred for 1.5 hours on a hot bath controlled to 100° C. The reaction mixture was concentrated under reduced pressure, and the residue was poured into ice water and extracted with ethyl acetate. The resultant organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatagraphy on silica gel (ethyl acetate:hexane=1:19) and crystallized from diethyl ether-hexane to obtain the title compound (1.6 g).

Workup

  1. temperatureThe mixture was heated
  2. customcontrolled to 100° C
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was poured into ice water
  5. extractionextracted with ethyl acetate
  6. washThe resultant organic layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by column chromatagraphy on silica gel (ethyl acetate:hexane=1:19)
  10. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-96f68103cf6446ae903a6a1f93e12c11
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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