6-Bromoimidazo[1,2-a]pyridine Chemical Properties

Melting point:

76-78 °C

Boiling point:

165 °C(Press: 1.5 Torr)

Density 

1.69±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

5.10±0.50(Predicted)

form 

crystalline needles

color 

Faint beige

Water Solubility 

slightly soluble in water.

InChI

InChI=1S/C7H5BrN2/c8-6-1-2-7-9-3-4-10(7)5-6/h1-5H

InChIKey

FXPMFQUOGYGTAM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

6188-23-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

2933998090

6-Bromoimidazo[1,2-a]pyridine Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

It is used in organic syntheses and as pharmaceutical intermediates. The best results were obtained with lactams that could be introduced on the 6-bromoimidazo[1,2-a]pyridine. 1,2-dihydro-5-imidazo [1,2-a]pyridin-6-yl-6-methyl-2-oxo-3-pyridinecarbonitrile hydrochloride monohydrate 6 was synthesized in 5 steps from 6-bromoimidazo[1,2-a] pyridine using [2- 14 C] cyanoacetamide as the source of the radiolabel.

Synthesis

(1) Preparation of 6-bromoimidazo[1,2-a]pyridine (4): 2.00 g of 2-amino-5-bromopyridine (3) was dissolved in 35 mL of ethanol, and 2.52 mL of 6.1 mol/L aqueous chloroacetaldehyde solution was added. The reaction mixture was heated to reflux for 3 hours. After completion of the reaction, the reaction mixture was concentrated and saturated aqueous NaHCO3 solution was added to the residue and extracted with ethyl acetate. After conventional post-treatment, 2.30 g of 6-bromoimidazo[1,2-a]pyridine was obtained as a brown powder (yield: 100%).LCMS (ESI) m/z (M + H)+: 368.93.

References

[1] Patent: US2011/98471, 2011, A1. Location in patent: Page/Page column 56
[2] Patent: US2014/134133, 2014, A1. Location in patent: Paragraph 0399
[3] Patent: WO2012/116237, 2012, A2. Location in patent: Page/Page column 118
[4] Patent: US2015/320727, 2015, A1. Location in patent: Paragraph 0553; 0554
[5] Patent: WO2008/14219, 2008, A2. Location in patent: Page/Page column 44-45

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