[1,2,4]Triazolo[1,5-a]pyridine-6-carboxaldehyde (9CI) Chemical Properties

Melting point:

156-158

Density 

1.39±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

1.57±0.30(Predicted)

Appearance

Light yellow to yellow Solid

InChIKey

SYLGZKAGHAOGFM-UHFFFAOYSA-N

Safety Information

WGK Germany 

3

HS Code 

2933399990

[1,2,4]Triazolo[1,5-a]pyridine-6-carboxaldehyde (9CI) Usage And Synthesis

Synthesis

General procedure for the synthesis of [1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde from N,N-dimethylformamide: (a) A solution of 6-iodo-[1,2,4]triazolo[1,5-a]pyridine (5.0 g) was prepared by dissolving 2-amino-5-iodopyridine (20 mmol) in anhydrous THF (300 mL) at 0 °C and slowly adding THF solution of isopropylmagnesium bromide (1M, 31 mL, 31 mmol). The resulting emulsion suspension was stirred at 0 °C for 1 h. DMF (6 mL, 50 mmol) was added. The suspension was allowed to warm up to room temperature and stirring was continued for 4 hours. Subsequently, 100 mL of water was added at room temperature and stirred for 1 hour. The reaction mixture was extracted with diethyl ether and washed with saturated Na2CO3 solution. The organic phase was dried with MgSO4 and concentrated. The residue was purified by silica gel short column chromatography using EtOAc as eluent to afford [1,2,4]triazolo[1,5-a]pyridine-6-carboxaldehyde as a light yellow solid (3 g, 100% yield). ESI-MS m/z: 148.0 [M+H]+. 1H NMR (CDCl3, 300MHz) δ: 10.03 (s, 1H), 9.10 (s, 1H), 8.49 (s, 1H), 8.02 (d, 1H), 7.82 (d, 1H).

References

[1] Patent: US2006/63809, 2006, A1. Location in patent: Page/Page column 17

[1,2,4]Triazolo[1,5-a]pyridine-6-carboxaldehyde (9CI)(614750-81-1)Related Product Information

• [1,2,4]TRIAZOLO[1,5-A]PYRIDINE-6-CARBONITRILE
• [1,2,4]Triazolo[1,5-a]pyridin-6-amine
• methyl [1,2,4]triazolo[1,5-a]pyridine-7-carboxylate
• [1,2,4]TRIAZOLO[1,5-A]PYRIDIN-8-AMINE
• [1,2,4]Triazolo[1,5-a]pyridine-2-carbaldehyde
• [1,2,4]Triazolo[4,3-a]pyridin-6-ylamine
• methyl [1,2,4]triazolo[1,5-a]pyridine-6-carboxylate
• [1,2,4]triazolo[1,5-a]pyridine-8-carbonitrile
• [1,2,4]triazolo[1,5-a]pyridin-8-ol
• 1,2,4-Triazolo[4,3-a]pyridin-8-amine
• [1,2,4]triazolo[1,5-a]pyridine-7-carbaldehyde
• [1,2,4]Triazolo[1,5-a]pyridine-5-carboxylic acid methyl ester
• [1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid
• [1,2,4]Triazolo[1,5-a]pyridine-7-carboxylic acid
• methyl [1,2,4]triazolo[1,5-a]pyridine-8-carboxylate
• [1,2,4]Triazolo[1,5-a]pyridine-6-MethanaMine
• [1,2,4]Triazolo[1,5-a]pyridine-6-carboxaldehyde (9CI)
• 2-ISOPROPYL-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE-6-CARBALDEHYDE