5-Bromo-2-(trifluoromethyl)pyridine → HCID 67252604, compound

HRID 2042048Notes

Reaction equation

HRID 2042048 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].CC(C)([O-])C.[K+].Br[C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][CH:22]=1>CC(N(C)C)=O.O>[F:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][C:17]2[CH:22]=[N:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=[CH:3][C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 135191803-Amino-4-fluorophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 67252604HCID 67252604, compoundYield 26.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
75 °C

Procedure

In DMA (8 mL) was placed 3-amino-4-fluorophenol (281 mg, 2.21 mmol), potassium t-butoxide (248 mg, 2.21 mmol) and 5-bromo-2-(trifluoromethyl)pyridine (500 mg, 2.21 mmol). The mixture was warmed to 75° C. overnight, then cooled to RT and diluted with water (75 mL). The mixture was extracted with ethyl acetate (2×40 mL) and the combined organic phases washed with brine (40 mL), dried (Na2SO4), concentrated in vacuo and purified by column chromatography to yield 2-fluoro-5-(6-(trifluoromethyl)pyridin-3-yloxy)benzenamine (161 mg, 26% yield) as an oil which was used without further purification. MS (ESI) m/z: 273.0 (M+H+).

Workup

  1. temperaturecooled to RT
  2. extractionThe mixture was extracted with ethyl acetate (2×40 mL)
  3. washthe combined organic phases washed with brine (40 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-8ec836ac029e40779119236ebc160be3
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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