Water → 3-[(Carbethoxymethyl)thio]-2-carbethoxyindole

HRID 2307912Notes

Reaction equation

HRID 2307912 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[SH:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:21]([O:20][C:18]([CH2:17][S:16][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:19])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 4715017Ethyl 3-Bromoindole-2-carboxylate

Product 1

HCID 150082093-[(Carbethoxymethyl)thio]-2-carbethoxyindoleYield 21%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl 3-bromoindole-2-carboxylate (1.34 g) and ethyl 2-mercaptoacetate (0.96 ml) in acetone (15 ml) was added potassium carbonate (1.38 g) and the resulting mixture was heated at reflux under argon for 18 hours. The cooled mixture was poured into water and extracted with ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated to a gum which was purified by column chromatography using iso-hexane:ethyl acetate (1:4) to give the desired product (331 mg, 21%) NMR d (CDCl3) 1.05 (t, 3H), 1.45 (t, 3H), 3.6 (s, 2H), 4.0 (q, 2H), 4.5 (q, 2H), 7.2-7.4 (m, 3H), 7.9 (d, 1H), 9.2 (brs, 1H); M/z (+) 308.3 (MH30).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux under argon for 18 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialCombined organic extracts were dried (MgSO4)
  5. concentrationconcentrated to a gum which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-69a47af91f594f53884c4a26a90cfe71
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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