IMidazo[1,2-a]pyridine,6-Methoxy-

IMidazo[1,2-a]pyridine,6-Methoxy- Property

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

6.28±0.50(Predicted)

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

IMidazo[1,2-a]pyridine,6-Methoxy- Chemical Properties,Usage,Production

Uses

6-Methoxyimidazo[1,2-a]pyridine are?imidazopyridines. This class of compounds are suggested to?inhibit?interleukin-1 receptor-associated kinase 4 (IRAK-4), which is a protein kinase involved in the signalling of innate immune response from Toll-like receptors (TLR). It can also be used to synthesize c-Met Inhibitors that have potential therapeutic applications for cancer treatment.

Synthesis

General procedure for the synthesis of 6-methoxyimidazo[1,2-a]pyridine from methanol and 6-iodoimidazo[1,2-a]pyridine: In a solvent mixture of toluene (10 mL) and methanol (5 mL), 6-iodoimidazo[1,2-a]pyridine (1.0 g, 4.1 mmol) was added. After allowing to dissolve, copper(I) iodide (160 mg, 0.84 mmol), 1,10-phenanthroline (300 mg, 1.66 mmol) and cesium carbonate (3 g, 9 mmol) were added sequentially. The reaction mixture was stirred and reacted at 120 °C overnight. After completion of the reaction, it was cooled to room temperature and extracted by adding water and ethyl acetate. The organic layer was separated, washed sequentially with water and saturated saline and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (eluent ratio: hexane:ethyl acetate:methanol, 50:50:0 → 0:100:0 → 0:95:5, v/v) to afford the target compound 6-methoxyimidazo[1,2-a]pyridine (360 mg, 59% yield).1H-NMR (CDCl3) δ: 3.82 (3H s), 6.96 (1H, dd, J = 9.6, 2.3 Hz), 7.50 (1H, d, J = 9.6 Hz), 7.52 (1H, s), 7.57 (1H, s), 7.66 (1H, d, J = 2.3 Hz).

References

[1] Patent: EP2565185, 2013, A1. Location in patent: Paragraph 0184