Sodium Chloride → 5-(2,4-Difluoro-phenylsulfanyl)-2-methanesulfonyl-6-methoxy-quinoline

HRID 1825857

Reaktionsgleichung

Reaktionsgleichung von HRID 1825857
[CH3:1][S:2]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[N:6]=1)(=[O:4])=[O:3].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[SH:25].C1C=CC(I(OC(C(F)(F)F)=O)OC(C(F)(F)F)=O)=CC=1.[Na+].[Cl-]>>[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[S:25][C:11]1[C:10]([O:15][CH3:16])=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]=[CH:14][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[N:6]2

Komponenten

5

Edukt 4

HCID 5234Sodium ChlorideHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 27370732,4-Difluorobenzene-1-thiolHCID 112533772-Methanesulfonyl-6-methoxy-quinoline

Produkt 1

HCID 98647125-(2,4-Difluoro-phenylsulfanyl)-2-methanesulfonyl-6-methoxy-quinoline

Versuchsvorschrift

A solution of 2-methanesulfonyl-6-methoxy-quinoline (237 mg , 1 mmole) and 2,4-difluorobenzenethiol (296 mg ,2 mmoles) was treated with PIFA (645 mg, 1. 5 mmoles) and stirred for 30 min. The solution was poured into dilute NaCl solution and extracted with ethyl acetate (EtOAc). The organic layer was dried (MgSO4) and evaporated. The resulting oil was crystallized to yield 5-(2,4-difluoro-phenylsulfanyl)-2-methanesulfonyl-6-methoxy-quinoline 101.; ([M+H]+)=382 The yield is typically 80–90%.

Aufarbeitung

  1. extractionextracted with ethyl acetate (EtOAc)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customThe resulting oil was crystallized

Quellen und Nachweise

ORD-Eintrag
ord-c470e275b06741a19f93245f94353303
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049325B2

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