Sodium Hydroxide → Methyl 6-[2,6-difluoro-4-(methylsulfonyl)phenyl]-5-fluoropyridine-2-carboxylate

HRID 1499561Notes

Reaction equation

HRID 1499561 reaction equation
[F:1][C:2]1[CH:7]=[C:6](SC)[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].[CH:22]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:33][S:34]([O-:37])(=S)=O.[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([S:34]([CH3:22])(=[O:37])=[O:33])[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

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 66652477Methyl 6-(2,6-difluoro-4-(methylthio)phenyl)-5-fluoropicolinate

Product 1

HCID 66652791Methyl 6-[2,6-difluoro-4-(methylsulfonyl)phenyl]-5-fluoropyridine-2-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 6-[2,6-difluoro-4-(methylthio)phenyl]-5-fluoropyridine-2-carboxylate (81.0 mg, 0.258 mmol) in DCM (1.2 mL) at 0° C. was added mCPBA (185 mg, 0.827 mmol). The reaction mixture was stirred at 0° C. for 2 h, followed by the addition of Na2S2O3 solution and then 1 M NaOH. The reaction mixture was stirred for 20 min. at room temperature, then extracted with DCM three times. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give the sub-title compound (78 mg, 87%). LCMS calc. for C14H11F3NO4S (M+H)+: m/z=346.0. Found: 346.2.

Workup

  1. stirringThe reaction mixture was stirred for 20 min. at room temperature
  2. extractionextracted with DCM three times
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-34990fd28456422fbea1354cc6da785f
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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