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

HRID 586277Notes

Reaction equation

HRID 586277 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, and the solvent was stripped at reduced pressure to afford 3-(3,5-difluoropyridin-2-yl)-4-fluorophenylamine, which was used subsequently without further purification: MS (ES+) m/z 225 [M+H]+.

Workup

  1. customwas indicated by TLC (0.25 to 3.5 h)
  2. customThe catalyst was then removed by filtration

Sources & evidence

ORD record
ord-d793b52b22fd4e6eb7c4e93944679318
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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