6-CHLOROIMIDAZO[1,2-A]PYRIDINE Chemical Properties

Melting point:

85-87°C

Boiling point:

132°C/1.5mmHg(lit.)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

5.18±0.50(Predicted)

color 

Light yellow to Yellow to Orange

InChI

InChI=1S/C7H5ClN2/c8-6-1-2-7-9-3-4-10(7)5-6/h1-5H

InChIKey

XQEGYCZJSVFGEE-UHFFFAOYSA-N

SMILES

C12=NC=CN1C=C(Cl)C=C2

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

6-CHLOROIMIDAZO[1,2-A]PYRIDINE Usage And Synthesis

Uses

6-Chlorimidazo[1,2-A]pyridine is a pyridine derivative and can be used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 6-chloroimidazo[1,2-A]pyridine from chloroacetaldehyde and 2-amino-5-chloropyridine: 2-amino-5-chloropyridine (4.50 g, 35.00 mmol) and 2-chloroacetaldehyde (10.30 g, 52.50 mmol, 8.45 mL) in a solvent mixture of ethanol (50.00 mL) and water (10 mL) were reacted at 80 °C The reaction was stirred for 16 hours. Upon completion of the reaction, the reaction solution was concentrated to dryness and the resulting residue was diluted with water (100 mL) and subsequently extracted with ethyl acetate (150 mL x 2). The organic phases were combined, washed sequentially with water (50 mL × 2) and saturated saline (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to afford 6-chloroimidazo[1,2-A]pyridine (5.10 g, 33.43 mmol) as a solid product. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δH 8.18 (d, 1H), 7.65 (s, 1H), 7.59-7.50 (m, 2H), 7.12 (dd, 1H).

References

[1] Patent: WO2018/98500, 2018, A1. Location in patent: Page/Page column 80; 81

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