Potassium peroxymonosulphate → Methyl 6-(2,6-difluoro-4-(methylsulfinyl)phenyl)-5-fluoropicolinate

HRID 1499555Notes

Reaction equation

HRID 1499555 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:12]=1[F:21].S([O-])(O[O-])(=O)=[O:23].[K+].[K+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:9])=[O:23])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:12]=1[F:21]

Participants

4

Reactant 2

HCID 10313463Potassium peroxymonosulphateHCID 66652477Methyl 6-(2,6-difluoro-4-(methylthio)phenyl)-5-fluoropicolinate

Product 1

HCID 70655092Methyl 6-(2,6-difluoro-4-(methylsulfinyl)phenyl)-5-fluoropicolinateYield 23.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 6-[2,6-difluoro-4-(methylthio)phenyl]-5-fluoropyridine-2-carboxylate (150 mg, 0.479 mmol) in DCM (3.0 mL) was added potassium peroxymonosulfate (147 mg, 0.958 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The solution was partitioned between EtOAc and water. The organic layer was dried, filtered. The filtrate was concentrated and then purified by silica gel column chromatography using CombiFlash® (0 to 100% EtOAc in hexanes) to give the sub-title compound as a white powder (37 mg, 23%). LCMS calc. for C14H11F3NO3S (M+H)+: m/z=330.0. Found: 330.2.

Workup

  1. customThe solution was partitioned between EtOAc and water
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-0469b486c1ca45c284decceab0b7368a
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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