Imidazo[1,2-a]pyridine-6-boronic acid Chemical Properties

Melting point:

115-117

Density 

1.31±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

7.99±0.43(Predicted)

form 

powder

color 

Pale Cream

InChI

InChI=1S/C7H7BN2O2/c11-8(12)6-1-2-7-9-3-4-10(7)5-6/h1-5,11-12H

InChIKey

IPJIKGJKMCILGV-UHFFFAOYSA-N

SMILES

B(C1=CN2C=CN=C2C=C1)(O)O

CAS DataBase Reference

913835-63-9

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Keep Cold

HS Code 

2934100090

Imidazo[1,2-a]pyridine-6-boronic acid Usage And Synthesis

Uses

Imidazo[1,2-a]pyridine-6-boronic acid is a useful intermediate for organic synthesis and other pharmaceutical processes.

Synthesis

Tricyclohexylphosphine (2.85 g, 0.010 mol), tris(dibenzylideneacetone)dipalladium (4.65 g, 0.005 mol), and 25.0% of the total amount of the reaction flask were added to the reaction flask under argon protection using 6-bromoimidazo[1,2-a]pyridine (20.0 g, 0.102 mol) and pinacol bis(dibenzylideneacetone) (38.7 g, 0.152 mol) as the starting material. sodium acetate. Subsequently, 1,4-dioxane (200 mL) was added as a solvent and the reaction mixture was heated to 115-120°C and stirred for 24 hours. After the reaction was completed, it was cooled to room temperature and diluted with purified water (200 mL). The reaction mixture was extracted with ethyl acetate (200 mL x 2), the organic phases were combined and dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give a reddish brown solid. The solid was dissolved in tert-butyl methyl ether (30 mL) and stirred at room temperature for 2 hours. The light yellow solid was collected by filtration to give imidazo[1,2-a]pyridine-6-boronic acid (11.8 g, 72.0% yield).

References

[1] Patent: CN106349246, 2017, A. Location in patent: Paragraph 0023; 0026; 27

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