4-Fluoroaniline → 5-Bromo-N-(4-fluorophenyl)pyridin-2-amine

HRID 238302Notes

Reaction equation

HRID 238302 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.[Na].C([O-])(C)(C)C>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:14][C:13]2[CH:15]=[CH:16][C:10]([F:9])=[CH:11][CH:12]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 97314-FluoroanilineHCID 693532,5-DibromopyridineHCID 131726539HCID 131726539, compound

Product 1

HCID 534107245-Bromo-N-(4-fluorophenyl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

5 g (21.1 mmol) of 2,5-dibromopyridine, 4.4 ml of 4-fluoroaniline, 4.10 g (42.3 mmol) of sodium-tert-butanolate, 200 mg (0.8 mmol) of palladium(II)acetate and 200 mg (0.3 mmol) of R-(+)-BINAP were dissolved in 60 ml of dioxane and stirred at reflux temperature for 1 h. The mixture was poured into ice-water and extracted with ethyl acetate. The organic phases were dried and evaporated, and the residue was purified by column chromatography (silica gel, n-heptane/ethyl acetate 5:2). Yield: 2.10 g.

Workup

  1. temperatureat reflux temperature for 1 h
  2. extractionextracted with ethyl acetate
  3. customThe organic phases were dried
  4. customevaporated
  5. customthe residue was purified by column chromatography (silica gel, n-heptane/ethyl acetate 5:2)

Sources & evidence

ORD record
ord-d21aae93e1e6420494fc2eb7c6248d57
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

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