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

HRID 456988

Reaktionsgleichung

Reaktionsgleichung von HRID 456988
[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-0466bb86afb243ab8565a782628806f3
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186840B2

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