Methanol → Methyl 3,5-difluoropyridine-2-carboxylate

HRID 1691673Notes

Reaction equation

HRID 1691673 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[C:7]([C:13]([OH:15])=[O:14])=[N:8][CH:9]=[C:10]([F:12])[CH:11]=1.[CH3:16]O>>[F:5][C:6]1[C:7]([C:13]([O:15][CH3:16])=[O:14])=[N:8][CH:9]=[C:10]([F:12])[CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27832623,5-Difluoropyridine-2-carboxylic acid

Product 1

HCID 46311137Methyl 3,5-difluoropyridine-2-carboxylate

Procedure

To 10 mL of methanol was added dropwise 2.5 mL of thionylchloride under cooling in an ice bath over 30 minutes. To the reaction mixture was added 500 mg of 3,5-difluoropyridine-2-carboxylic acid, and warmed to room temperature, followed by stirring for 3 days. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. After filtration, it was concentrated under reduced pressure to obtain 496 mg of methyl 3,5-difluoropyridine-2-carboxylate.

Workup

  1. temperatureunder cooling in an ice bath over 30 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona saturated aqueous sodium hydrogen carbonate solution was added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration, it
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-07f7604acad843609e4a6a2cfe366713
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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