Bis(trifluoroacetoxy)iodobenzene → 3-(2,4-Difluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester

HRID 2218230

Reaction equation

HRID 2218230 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:8]=2)([O:3][CH3:4])=[O:2].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[SH:26].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>[CH3:4][O:3][C:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[S:26][C:20]1[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=1[F:18])=[CH:11][CH:10]=[C:9]([S:14]([CH3:17])(=[O:15])=[O:16])[CH:8]=2)=[O:2]

Participants

5

Reactant 3

HCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 27370732,4-Difluorobenzene-1-thiolHCID 7141904methyl 6-(methylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 114180743-(2,4-Difluoro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxylic acid methyl esterYield 88%

Reagents, catalysts & solvents 1

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

Procedure

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.

Workup

  1. customthen partitioned between methylene chloride and water
  2. customAfter concentration of the methylene chloride layer to 20 mL the product was precipitated by addition of 30 mL hexane

Sources & evidence

ORD record
ord-190b6e9a69a34ddd8ee3cf03be2beac6
Source dataset
uspto-grants-2008_08
Patent number
US07410994B2

Linked notes

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