6-(Methylthio)-1H-indole-2-carboxylic acid → 6-(Methylsulfanyl)-1H-indole

HRID 442752Notes

Reaction equation

HRID 442752 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8](C(O)=O)[NH:9]2)=[CH:5][CH:4]=1>N1C2C(=CC=CC=2)C=CC=1>[CH3:1][S:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 39071736-(Methylthio)-1H-indole-2-carboxylic acid

Product 1

HCID 198489176-(Methylsulfanyl)-1H-indoleYield 90.6%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Conditions

Temperature
215 °C

Procedure

A mixture of 6-methylsulfanyl-1H-indole-2-carboxylic acid (9.6 g, 46 mmol), Cu powder (2.1 g, 33 mmol) and quinoline (100 ml) was heated at 215° C. for 3 hours. The mixture was cooled to room temperature, filtered through celite, and the filtrate diluted with H2O (500 mL). The cooled mixture was acidified with concentrated HCl (pH=1), and extracted with EtOAc. The organic fraction was washed with saturated NaCl solution, dried over MgSO4, filtered and evaporated to give of 6-Methylsulfanyl-1H-indole (6.8 g, 90%) after purification by flash column chromatography.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through celite
  3. additionthe filtrate diluted with H2O (500 mL)
  4. extractionextracted with EtOAc
  5. washThe organic fraction was washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-1e46f9022ba945e697bdd1f5b670b94d
Source dataset
uspto-grants-1999_04
Patent number
US05891901

Reaction notes

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