HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bis(trifluoroacetoxy)iodobenzene → 3-(2,4-Difluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bis(trifluoroacetoxy)iodobenzene | HCID 102317 | — |
| Reactant | 2,4-Difluorobenzene-1-thiol | HCID 2737073 | — |
| Reactant | methyl 6-(methylsulfonyl)-1H-indole-2-carboxylate | HCID 7141904 | — |
| Solvent | 1,1,1,3,3,3-Hexafluoro-2-propanol | HCID 13529 | — |
| Product | 3-(2,4-Difluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester | HCID 11418074 | 88% |
Reaction Steps
A solution of 2-carbomethoxy-6-methylsulfonylindole (750 mg, 2.8 mmol), in 10 mL hexafluoroisopropanol was treated with 2,4-difluorothiophenol (7.5 mmol) followed by addition of PIFA (5.6 mmol). The dark colored solution was stirred overnight then partitioned between methylene chloride and water. After concentration of the methylene chloride layer to 20 mL the product was precipitated by addition of 30 mL hexane. An 88% yield of 3-(2,4-difluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07074939B2 |
| Source dataset | uspto-grants-2006_07 |
| ORD ID | ord-523b1051d6cf45ca941f7f0badcea3ce |
| Source note | uspto-grants-2006_07 |