Ethanol → 3-(3,5-Difluoropyridin-2-yl)-4-fluorophenylamine

HRID 1061810Notes

Reaction equation

HRID 1061810 reaction equation
Br[C:2]1[C:7]([F:8])=[C:6](Br)[C:5]([F:10])=[C:4]([C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=2[F:20])[N:3]=1.C(N(CC)CC)C.C(O)C>ClCCl.[Pd]>[F:10][C:5]1[C:4]([C:11]2[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:12]=2[F:20])=[N:3][CH:2]=[C:7]([F:8])[CH:6]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 222852742,4-Dibromo-3,5-difluoro-6-(2-fluoro-5-nitrophenyl)pyridine

Product 1

HCID 222852913-(3,5-Difluoropyridin-2-yl)-4-fluorophenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2,4-dibromo-3,5-difluoro-6-(2-fluoro-5-nitrophenyl)pyridine (1.20 g, 2.91 mmol) dissolved in dichloromethane (30 mL) was added triethylamine (3 mL) and ethanol (80 mL) followed by 10% palladium on carbon (0.536 g). The mixture was then shaken under an atmosphere of hydrogen gas at 45 psi until complete reaction was indicated by TLC (0.25 to 3.5 h). The catalyst was then removed by filtration through glass microfibre filter paper (GF/A) and the solvent stripped at reduced pressure to afford 3-(3,5-difluoropyridin-2-yl)-4-fluorophenylamine which was used subsequently without further purification: m/z (ES+) 225 (MH+).

Workup

  1. customwas indicated by TLC (0.25 to 3.5 h)
  2. customThe catalyst was then removed by filtration through glass microfibre
  3. filtrationfilter paper (GF/A)

Sources & evidence

ORD record
ord-1793f9f7f5c046f4a34d87e39f902495
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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