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

HRID 2218230

Reaktionsgleichung

Reaktionsgleichung von HRID 2218230
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-190b6e9a69a34ddd8ee3cf03be2beac6
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07410994B2

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