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

HRID 410210Notes

Reaction equation

HRID 410210 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[F:13][C:8]1[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 1

HCID 593267823-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine

Product 1

HCID 593271552-Fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottomed flask was added 3-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine (3.5962 g, 20.07 mmol) and palladium hydroxide on carbon (1.409 g, 2.007 mmol) in EtOAc (66.9 mL). The round bottomed flask was flushed with argon and then placed under vacuum three times. A hydrogen balloon was then attached to the reaction. Upon completion, the reaction was filtered through celite to produce 2-Fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine. MS (ESI, pos. ion) m/z: 182.1 (M+1).

Workup

  1. customThe round bottomed flask was flushed with argon
  2. customA hydrogen balloon was then attached to the reaction
  3. filtrationUpon completion, the reaction was filtered through celite

Sources & evidence

ORD record
ord-4a1b44b3bee5405eb6eca29bb7581943
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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