Iodine → {3-[(2,6-Dichlorophenyl)sulfanyl]-2,5-dimethyl-1H-indol-1-yl}acetic acid

HRID 2240563Notes

Reaction equation

HRID 2240563 reaction equation
II.[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[SH:11].COC1C=CC(S([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([CH3:32])[CH:30]=3)[N:25]([CH2:33][C:34]([OH:36])=[O:35])[C:24]=2[CH3:37])(=O)=O)=CC=1>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[S:11][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH3:32])[CH:30]=2)[N:25]([CH2:33][C:34]([OH:36])=[O:35])[C:24]=1[CH3:37]

Participants

5

Reactant 3

HCID 807IodineHCID 90671Benzenethiol, 2,6-dichloro-HCID 10067946HCID 10067946, compound

Product 1

HCID 21077814{3-[(2,6-Dichlorophenyl)sulfanyl]-2,5-dimethyl-1H-indol-1-yl}acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodine (0.51 g) was added to a solution of 2,6-dichlorobenzenethiol (0.36 g) and the product from example 13 step a) (0.2 g) in DMF (5 ml). After 1 h the solution was purified by reverse phase HPLC. The solvent was evaporated in vacuo and the oily residue treated with ether to give a solid. Filtered off and dried to yield the title compound as a white solid (0.22 g).

Workup

  1. customAfter 1 h the solution was purified by reverse phase HPLC
  2. customThe solvent was evaporated in vacuo
  3. additionthe oily residue treated with ether
  4. customto give a solid
  5. filtrationFiltered off
  6. customdried

Sources & evidence

ORD record
ord-9750378e5b2741299c06a7a2fdd51547
Source dataset
uspto-grants-2010_05
Patent number
US07723373B2

Reaction notes

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