3-(2,5-Dihydrofuran-2-yl)-2-fluoropyridine → 2-Fluoro-3-(tetrahydrofuran-2-yl)pyridine

HRID 1517593Notes

Reaction equation

HRID 1517593 reaction equation
[O:1]1[CH2:5][CH:4]=[CH:3][CH:2]1[C:6]1[C:7]([F:12])=[N:8][CH:9]=[CH:10][CH:11]=1>CO.[Pd]>[F:12][C:7]1[C:6]([CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 1

HCID 671676503-(2,5-Dihydrofuran-2-yl)-2-fluoropyridine

Product 1

HCID 671680662-Fluoro-3-(tetrahydrofuran-2-yl)pyridineYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A round-bottom flask containing 3-(2,5-dihydrofuran-2-yl)-2-fluoropyridine (170 mg, 1 mmol) and 10% Pd/C in methanol (3.1 mL) is evacuated under vacuum and filled with hydrogen with the aid of a balloon. The reaction is stirred overnight at room temperature and filtered over celite. The solvent is evaporated in vacuo to give 148 mg of 2-fluoro-3-(tetrahydrofuran-2-yl)pyridine. MS (m/z): 168 (M+1).

Workup

  1. customis evacuated under vacuum
  2. additionfilled with hydrogen with the aid of a balloon
  3. filtrationfiltered over celite
  4. customThe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-c7f34726c7cc4286a571c2928920ef14
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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