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

HRID 1392761Notes

Reaction equation

HRID 1392761 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 chromatography 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 chromatography on silica gel (ethyl acetate:hexane=1:19)
  10. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-26857090806a4522883316da6e54a2b6
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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