HCID 59327230, compound → 2-Fluoro-3-(tetrahydrofuran-3-YL)pyridine

HRID 1880159Notes

Reaction equation

HRID 1880159 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]([C:6]2[C:7]([F:12])=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:2]1>C1COCC1.[OH-].[Pd+2].[OH-]>[F:12][C:7]1[C:6]([CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 1

HCID 59327230HCID 59327230, compound

Product 1

HCID 593272332-Fluoro-3-(tetrahydrofuran-3-YL)pyridine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(2,3-dihydrofuran-3-yl)-2-fluoropyridine (5.26 g, 31.8 mmol) and palladium hydroxide, 20 wt % pd (dry basis) on carbon, wet (2.500 g, 3.56 mmol) in THF (50 mL) was evacuated/purged with hydrogen (3×). The mixture was stirred vigorously under hydrogen (1 atm) at rt overnight. The mixture was filtered through a pad of Celite and the filtrate was concentrated to dryness to give a clear colorless oil. MS (ESI, pos. ion) m/z: 168.1 (M+1).

Workup

  1. customwas evacuated/purged with hydrogen (3×)
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated to dryness
  4. customto give a clear colorless oil

Sources & evidence

ORD record
ord-cda29c19338f4f898cdb2f4d44cf21ab
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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