Ethanol → 5-Fluoro-4-(1-methylpiperidin-4-yl)pyridin-3-amine

HRID 524954Notes

Reaction equation

HRID 524954 reaction equation
[F:1][C:2]1[C:3]([C:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH:14]=2)=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.CCO>CCOC(C)=O.[Pd]>[F:1][C:2]1[C:3]([CH:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 867210095-fluoro-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)pyridin-3-amine

Product 1

HCID 867210105-Fluoro-4-(1-methylpiperidin-4-yl)pyridin-3-amineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

Pd on C, wet, Degussa (25 mg, 0.1175 mmol) was added to a stirred solution of 5-fluoro-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)pyridin-3-amine (61 mg, 0.2943 mmol) in EtOAc (5 mL)/EtOH (5 mL). The reaction was placed under an atmosphere of hydrogen and stirred at ambient temperature for 15 hours. A further portion of Pd on C, wet, Degussa (25 mg, 0.1175 mmol) was added and the reaction was placed under an atmosphere of hydrogen and stirred at ambient temperature for 24 hours. The catalyst was removed by filtration through a pad of celite and the filtrate concentrated in vacuo to give 5-fluoro-4-(1-methylpiperidin-4-yl)pyridin-3-amine as an off-white solid (58 mg, 95% Yield). MS (ES+) 210.1.

Workup

  1. stirringstirred at ambient temperature for 24 hours
  2. customThe catalyst was removed by filtration through a pad of celite
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e00382932b6f4c23ad952f9cc53428cb
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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