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

HRID 473640Notes

Reaction equation

HRID 473640 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-].[Pd+2].[OH-]>[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 rbf was added 3-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine (2.1320 g, 11.90 mmol) and palladium hydroxide (0.835 g, 1.190 mmol) in EtOAc (39.7 mL). The rbf 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 and concentrated. MS (ESI, pos. ion) m/z: 182.1.

Workup

  1. customThe rbf was flushed with argon
  2. customA hydrogen balloon was then attached to the reaction
  3. filtrationUpon completion, the reaction was filtered through celite and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b6fc864da81d4ad491a65e682696b86c
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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