3-(5,6-dihydro-2H-pyran-3-yl)-2-fluoropyridine → 2-fluoro-3-(tetrahydro-2H-pyran-3-yl)pyridine

HRID 410229Notes

Reaction equation

HRID 410229 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]=[C:3]([C:7]2[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:2]1>C1COCC1.[Pd]>[F:13][C:8]1[C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][O:1][CH2:2]2)=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 1

HCID 593270283-(5,6-dihydro-2H-pyran-3-yl)-2-fluoropyridine

Product 1

HCID 593269202-fluoro-3-(tetrahydro-2H-pyran-3-yl)pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium (0.005 g, 0.005 mmol, 10% wt. on activated carbon) was added to a stirred solution of 3-(5,6-dihydro-2H-pyran-3-yl)-2-fluoropyridine (0.10 g, 0.558 mmol) in THF (2 mL). The reaction mixture was placed under a hydrogen atmosphere (balloon) and stirred at room temperature for 4 h. The reaction mixture was filtered through Celite, and the filtrate was concentrated in vacuo to give 2-fluoro-3-(tetrahydro-2H-pyran-3-yl)pyridine. MS (ESI, pos. ion) m/z: 182.1 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-06d3880d0420427cab591c5bb0a7a20a
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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