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

HRID 1846751Notes

Reaction equation

HRID 1846751 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>CO.[Pd]>[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)pyridineYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(3,6-dihydro-2H-pyran-4-yl)-2-fluoro-pyridine (260 mg, 1.45 mmol) in MeOH (20 mL) was added Pd/C (0.1 g), bubbled with H2 and stirred at RT overnight. The reaction mixture was filtered and the filtrate was concentrated to give 2-fluoro-3-(tetrahydro-pyran-4-yl)-pyridine (250 mg, 1.38 mmol, 95.3% yield).

Workup

  1. custombubbled with H2
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-43598cd280e240c5b31a983d7968cf0f
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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