2-Propanethiol → 2-Isopropylthio-3-fluoropyridine

HRID 976228Notes

Reaction equation

HRID 976228 reaction equation
[CH:1]([SH:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].F[C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][N:13]=1>CN(C)C=O>[F:18][C:17]1[C:12]([S:4][CH:1]([CH3:3])[CH3:2])=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 11430Potassium CarbonateHCID 27831762,3-Difluoropyridine

Product 1

HCID 199667562-Isopropylthio-3-fluoropyridineYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

220.93 g of isopropyl mercaptan are added dropwise at a temperature of from 0° to -5° C. to a mixture of 388.6 g of potassium carbonate and 301 g of 2,3-difluoropyridine in 4300 ml of dimethylformamide. After stirring for 20 minutes, the temperature of the reaction mixture is allowed to rise slowly to room temperature and is stirred for a further 30 minutes. The reaction mixture is then added to an ice-water/ethyl acetate mixture, the phases are washed four times with ethyl acetate and ice-water and then dried over sodium sulfate. After filtering and concentrating by evaporation, the resulting crude product (510 g) is purified by column chromatography (ethyl acetated hexane 1:9) to give 327.3 g of 3-fluoro-2-isopropylthiopyridine in the form of an oil.

Workup

  1. customto rise slowly to room temperature
  2. stirringis stirred for a further 30 minutes
  3. washthe phases are washed four times with ethyl acetate and ice-water
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtering
  6. concentrationconcentrating by evaporation
  7. customthe resulting crude product (510 g) is purified by column chromatography (ethyl acetated hexane 1:9)

Sources & evidence

ORD record
ord-05595e0a834a414d8932ee983b6b8cf3
Source dataset
uspto-grants-1997_03
Patent number
US05612288

Reaction notes

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