HCID 86597543, compound → 3-(2-sulfanylethyl)-1H-indole-2-carboxylic acid

HRID 858281Notes

Reaction equation

HRID 858281 reaction equation
C([S:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]([O-:18])=[O:17])(=O)C>C1COCC1>[SH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]([OH:18])=[O:17]

Participants

3

Reactant 1

HCID 86597543HCID 86597543, compound

Product 1

HCID 101926883-(2-sulfanylethyl)-1H-indole-2-carboxylic acidYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a deoxygenated solution of 3-[2-(acetylthio)ethyl]-1H-indole-2-carboxylate (0.277 g, 1.0 mmol) in THF (5 mL) was added deoxygenated 0.5 N KOH (10 mL), and the mixture was stirred at room temperature under nitrogen for 20 hours. The volatile solvent was removed under reduced pressure and the resulting aqueous mixture was poured into a mixture of EtOAc/1 N HCl (10 mL/10 mL). The organic layer was dried over Na2SO4 and concentrated. The crude material was purified by silica gel chromatography (EtOAc/hexanes, 1/1) to give 0.150 g (0.68 mmol, 68% yield) of 3-(2-mercaptoethyl)-1H-indole-2-carboxylic acid as a white solid: 1H NMR (CDCl3) δ 1.49 (t, J=8.0 Hz, 1H), 2.91 (q, J=7.7 Hz, 2H), 3.48 (t, J=7.5 Hz, 2H), 7.19 (ddd, J=1.3, 6.6, and 8.1 Hz, 1H), 7.38 (t, J=7.4 Hz, 1H), 7.42 (d, J=8.1 Hz, 1H), 7.75 (d, J=8.1 Hz, 1H), 8.85 (s, 1H); 13C NMR (CDCl3) □ 25.4, 29.5, 112.0, 120.7, 121.1, 122.4, 124.7, 126.6, 127.9, 136.3, 167.0. Anal. Calcd. for C11H11NO2S: C, 59.71; H, 5.01; N, 6.33; S, 14.49. Found: C, 59.58; H, 5.07; N, 6.25; S, 14.28.

Workup

  1. customdeoxygenated 0.5 N KOH (10 mL)
  2. customThe volatile solvent was removed under reduced pressure
  3. additionthe resulting aqueous mixture was poured into a mixture of EtOAc/1 N HCl (10 mL/10 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography (EtOAc/hexanes, 1/1)

Sources & evidence

ORD record
ord-84cbff6793524b42924193f27f7d96a6
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

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