2-Bromo-5-fluoro-4-((1-methylpiperidin-4-yl)oxy)-3-nitropyridine → 5-Fluoro-4-((1-methylpiperidin-4-yl)oxy)pyridin-3-amine

HRID 524939Notes

Reaction equation

HRID 524939 reaction equation
Br[C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([O:11][CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[C:5]([F:19])=[CH:4][N:3]=1.[H][H]>CO.[Zn+2].[Br-].[Br-].[Pd]>[F:19][C:5]1[C:6]([O:11][CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[C:7]([NH2:8])[CH:2]=[N:3][CH:4]=1

Participants

6

Reactant 2

HCID 867209972-Bromo-5-fluoro-4-((1-methylpiperidin-4-yl)oxy)-3-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 867209985-Fluoro-4-((1-methylpiperidin-4-yl)oxy)pyridin-3-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 10421208Zinc bromideCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-bromo-5-fluoro-4-[(1-methyl-4-piperidyl)oxy]-3-nitro-pyridine (96 mg, 0.2873 mmol), ZnBr2 (12.94 mg, 3.080 μL, 0.05746 mmol) and Pd on C, wet, Degussa (31 mg) in methanol (5 mL) was flushed with hydrogen and evacuated (3×) and then stirred under a hydrogen atmosphere overnight. The catalyst was filtered off through a celite pad and washed with methanol and ethyl acetate mixtures and the filtrate was concentrated in vacuo to leave a pale yellow oil that was used in next step without further purification. MS (ES+) 226.1.

Workup

  1. customevacuated (3×)
  2. filtrationThe catalyst was filtered off through a celite pad
  3. washwashed with methanol and ethyl acetate mixtures
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto leave a pale yellow oil that
  6. customwas used in next step without further purification

Sources & evidence

ORD record
ord-8ba64bcbe6fe43dc9ebedbeb7598ba9b
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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