2-Pyridinemethanamine,5-fluoro-(9CI) Chemical Properties

Boiling point:

181.6±25.0 °C(Predicted)

Density 

1.180±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

8.30±0.39(Predicted)

form 

liquid

color 

Colourless

Safety Information

HS Code 

2933399990

2-Pyridinemethanamine,5-fluoro-(9CI) Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-fluoropyridine-2-methylamine from 2-cyano-5-fluoropyridine: 1. hydrogenation reaction: 2-cyano-5-fluoropyridine (63.2 g, 0.52 mol), nickel ruanne (22.5 g) and ammonia-saturated ethanol (1.5 L) were mixed and reacted at 70°C for 16 hours under 500 psi hydrogen pressure. 2. Purification: After completion of the reaction, the dark purple liquid was separated by fast silica gel column chromatography (eluent: dichloromethane/methanol/ammonium hydroxide = 95:4.5:0.5). Concentration gave the free base of 5-fluoropyridine-2-methylamine in yellow liquid in a yield of 25.0 g (44%). Characterization data: 1H NMR (DMSO-d6) δ 8.43 (d, J=2.9Hz, 1H), 7.66 (m, 1H), 7.50 (m, 1H), 3.77 (s, 2H), 2.10 (br, 2H); MS (ESI) m/z 127 (M+H). 3. Salt-forming reaction: the free base (20.0 g, 159.0 mmol) was dissolved in 1,4-dioxane (150 mL) and a dioxane solution (150 mL, 3.8 eq.) of 4N HCl was added to immediately precipitate a white solid. It was diluted with ether (300 mL) and filtered to give 5-fluoropyridine-2-methylamine dihydrochloride. 4. Drying: The product was dried at 20 mmHg, 60°C to give pure dihydrochloride in a yield of 30.0 g (95%). Characterization data: 1H NMR (DMSO-d6) δ 8.61 (d, J=2.9Hz, 1H), 8.50 (brs, 3H), 7.82 (m, 1H), 7.62 (m, 1H), 7.50 (br, 1H), 4.18 (m, 2H); MS (ESI) m/z 127 (M+H, free base).

References

[1] Patent: WO2005/66126, 2005, A1. Location in patent: Page/Page column 76
[2] Patent: WO2006/12374, 2006, A1. Location in patent: Page/Page column 214
[3] Patent: US2003/225106, 2003, A1. Location in patent: Page 95
[4] Patent: WO2013/30138, 2013, A1. Location in patent: Page/Page column 108; 109
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 9, p. 2793 - 2800

2-Pyridinemethanamine,5-fluoro-(9CI)(561297-96-9)Related Product Information

• 1-(5-CHLOROPYRIDIN-2-YL)METHANAMINE
• 2-Pyridinecarboximidamide,5-fluoro-N-hydroxy-
• 6-ACETYL-5-FLUOROPYRIDINE-2-CARBOXAMIDE
• 3-BROMO-5-FLUORO-6-METHOXYPYRIDINE-2-CARBOXAMIDE
• 3,5-DIFLUOROPYRIDINE-2-CARBOXAMIDE
• C-(5-FLUORO-3-METHYL-PYRIDIN-2-YL)-METHYLAMINE
• RARECHEM AL BW 2484