Water → N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-(methylamino)picolinamide

HRID 2360372Notes

Reaction equation

HRID 2360372 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[C:3]=1[NH:22][C:23](=[O:31])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26](Cl)[N:25]=1.[CH3:32][NH2:33].O.C(OCC)(=O)C>O1CCOCC1.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[C:3]=1[NH:22][C:23](=[O:31])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:33][CH3:32])[N:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 8857Ethyl AcetateHCID 86654246N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-chloropicoline amide

Product 1

HCID 86654248N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-(methylamino)picolinamideYield 69%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.100 g (0.180 mmol) of N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-6-chloropicoline amide in 5 ml of 1,4-dioxane were added 0.00600 g (0.0360 mmol) of copper sulfate and 0.140 g (1.80 mmol) of a 40% aqueous methylamine solution, followed by stirring at an oil bath temperature 80° C. for 3 hours under an enclosed condition. The reaction liquid was returned to room temperature and opened, and water and ethyl acetate were added thereto. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=2:1) to prepare 0.0700 g (yield 69%) of a target compound.

Workup

  1. customThe reaction liquid
  2. customwas returned to room temperature
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2693a2f1cbcf4481bf25865bae1db6ca
Source dataset
uspto-grants-2014_04
Patent number
US08686044B2

Reaction notes

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