4-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine → 2-fluoro-4-(tetrahydro-2H-pyran-4-yl)pyridine

HRID 1842518Notes

Reaction equation

HRID 1842518 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([F:13])[CH:8]=2)[CH2:3][CH2:2]1.[H][H]>CCO.[OH-].[Pd+2].[OH-]>[F:13][C:9]1[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 585484534-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 585484782-fluoro-4-(tetrahydro-2H-pyran-4-yl)pyridineYield 95.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of palladium hydroxide, (20 wt % palladium dry basis on carbon, wet, degussa type e101 ne/w, 150 mg), and 4-(3,6-Dihydro-2H-pyran-4-yl)-2-fluoropyridine (0.90 g, 5.0 mmol) in EtOH (10 mL) was placed under 1 atm hydrogen (balloon) and stirred for 4 h at RT. The mixture was then placed back under argon atmosphere, the palladium was filtered off, and the filtrate was concentrated to give 2-fluoro-4-(tetrahydro-2H-pyran-4-yl)pyridine (0.86 g, 4.76 mmol, 95%) as a yellow oil.

Workup

  1. filtrationthe palladium was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9e9829b4fd614181bb4397ca10bd38a1
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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