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

HRID 1880077Notes

Reaction equation

HRID 1880077 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-43b10ae843c1403691e1c917ea048d6e
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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