1,1,1-Trifluoro-3-iodopropane → 6-[(3,3,3-Trifluoropropyl)sulfanyl]pyridine-3-carboxylic acid

HRID 341558Notes

Reaction equation

HRID 341558 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[F:16][C:17]([F:22])([F:21])[CH2:18][CH2:19]I>CCO>[F:16][C:17]([F:22])([F:21])[CH2:18][CH2:19][S:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1561651,1,1-Trifluoro-3-iodopropaneHCID 517045Sodium AcetateHCID 1785245186-sulfanylpyridine-3-carboxylic acid

Product 1

HCID 645545626-[(3,3,3-Trifluoropropyl)sulfanyl]pyridine-3-carboxylic acidYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 6-sulfanylpyridine-3-carboxylic acid (0.5 g, 3.22 mmol) in EtOH (50 mL) at 0 C was added sodium acetate (0.26 g, 3.22 mmol) and 1,1,1-trifluoro-3-iodopropane (0.72 g, 3.22 mmol) and the mixture was heated at 80 C for 24 h. The mixture was concentrated under vacuum, water was added and the mixture was acidified to pH 4 using acetic acid. The resultant yellow precipitate was collected by filtration and purified by FCC, eluting with 2% MeOH in DCM to afford the title compound (0.459 g, 57%). Method B HPLC-MS: MH+ requires m/z=252 Found: m/z=252, Rt=1.84 min (91%).

Workup

  1. temperaturethe mixture was heated at 80 C for 24 h
  2. concentrationThe mixture was concentrated under vacuum, water
  3. additionwas added
  4. filtrationThe resultant yellow precipitate was collected by filtration
  5. custompurified by FCC
  6. washeluting with 2% MeOH in DCM

Sources & evidence

ORD record
ord-fb30a91997cf43c7aae5f6e5a2d7c7b9
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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