HCID 15729535, compound → HCID 67396307, compound

HRID 1426775Notes

Reaction equation

HRID 1426775 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](F)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][OH:17].C[O-].[Na+]>>[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:17][CH3:16])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 15729535HCID 15729535, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 67396307HCID 67396307, compoundYield 86%

Procedure

2-(Benzylthio)-6-fluoropyridine (199 mg) and 28% sodium methoxide methanol solution (2 mL) were stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as a yellow oil (yield 182 mg, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8f0ef5c92024cf88b5eac3ae7b762f5
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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