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

HRID 456988

Reaction equation

HRID 456988 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-0466bb86afb243ab8565a782628806f3
Source dataset
uspto-grants-2007_03
Patent number
US07186840B2

Linked notes

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