2-Cyano-5-fluoropyridine → (5-Fluoropyridin-2-yl)methanamine

HRID 887642Notes

Reaction equation

HRID 887642 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1>CO.Cl.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1

Participants

5

Reactant 1

HCID 113324532-Cyano-5-fluoropyridine

Product 1

HCID 45079543(5-Fluoropyridin-2-yl)methanamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

The mixture of 5-fluoro-pyridine-2-carbonitrile (0.16 g, 1.27 mmol) and Pd/C (0.030 g, 10% wt) in 15 ml of MeOH and 0.50 ml of concentrated HCl was placed under H2 which was provided by a balloon and stirred at RT for 4 h, filtered through Celite®, condensed, the residue was purified by flash column chromatography. The titled compound was obtained as a light yellowish solid. MS (ES+): 127.2 (free base)(M+H)+. Calc'd for C6H7FN2 (free base)—126.13.

Workup

  1. customwas provided by a balloon
  2. filtrationfiltered through Celite®, condensed
  3. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-0228a8820a5a43a1aaab5bb08b76cb27
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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