4-Fluorothiophenol → HCID 22034364, compound

HRID 1792158Notes

Reaction equation

HRID 1792158 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[C:10]([CH3:14])[NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.C1C=CC(I(OC(C(F)(F)F)=O)OC(C(F)(F)F)=O)=CC=1>FC(F)(F)C(O)C(F)(F)F>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:9]2[C:8]3[C:12](=[CH:13][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[NH:11][C:10]=2[CH3:14])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 677894-FluorothiophenolHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 11333276HCID 11333276, compound

Product 1

HCID 22034364HCID 22034364, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

A solution of 6-methanesulfonyl-2-methyl-1H-indole (207 mg, 1 mmol) in 6 mL of hexafluoroisopropanol was treated with 4-fluorothiophenol (2 mmol) followed by addition of PIFA (1.5 mmol). The dark colored solution was stirred for 30 minutes followed by partitioning between EtOAc and water. Purification by TLC (2:1 hexane/EtOAc) afforded 145 mg of 3-(4-fluoro-phenylsulfanyl)-6-methanesulfonyl-2-methyl-1H-indole, 101, MS: 336 ([M+H]+).

Workup

  1. customby partitioning between EtOAc and water
  2. customPurification by TLC (2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-528a8c9dd1f74cc2a0a17ba4243f5107
Source dataset
uspto-grants-2006_07
Patent number
US07074939B2

Reaction notes

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