7-bromoimidazo[1,5-a]pyridine

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7-bromoimidazo[1,5-a]pyridine Basic information
Product Name:7-bromoimidazo[1,5-a]pyridine
Synonyms:7-bromoimidazo[1,5-a]pyridine;Imidazo[1,5-a]pyridine, 7-bromo-;-Bromoimidazo[1,5-a]pyridine
CAS:865156-48-5
MF:C7H5BrN2
MW:197.03
EINECS:
Product Categories:
Mol File:865156-48-5.mol
7-bromoimidazo[1,5-a]pyridine Structure
7-bromoimidazo[1,5-a]pyridine Chemical Properties
density 1.69±0.1 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka6.02±0.30(Predicted)
AppearanceYellow to brown Solid
CAS DataBase Reference865156-48-5
Safety Information
MSDS Information
7-bromoimidazo[1,5-a]pyridine Usage And Synthesis
Uses7-Bromoimidazo[1,5-a]pyridine is used in the discovery of novel imidazopyridine GSK-3β inhibitors supported by computational approaches.
Synthesis
N-((4-bromopyridin-2-yl)methyl)formamide

865156-49-6

7-bromoimidazo[1,5-a]pyridine

865156-48-5

General procedure for the synthesis of 7-bromoimidazo[1,5-a]pyridine from N-((4-bromopyridin-2-yl)methyl)formamide: To a 100 mL round bottom flask was added a solution of N-((4-bromopyridin-2-yl)methyl)formamide (Compound 39.2, 3.0 g, 90%, 12.6 mmol) in dichloromethane (20 mL). The solution was cooled to 0-5 °C and then trifluoroacetic anhydride (1.93 mL, 13.9 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 1 h. Subsequently, the pH was adjusted to 7 by slow addition of saturated aqueous sodium carbonate solution. The aqueous phase was extracted with dichloromethane (3 x 20 mL), the organic layers were combined and washed with brine (3 x 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate/petroleum ether (1/1) as eluent to afford 7-bromoimidazo[1,5-a]pyridine as a brown solid.

References[1] Patent: WO2014/8197, 2014, A1. Location in patent: Page/Page column 106; 107
[2] Patent: WO2015/95767, 2015, A1. Location in patent: Page/Page column 121; 122
[3] Patent: WO2005/90305, 2005, A1. Location in patent: Page/Page column 29-30
[4] Patent: WO2005/90304, 2005, A1. Location in patent: Page/Page column 38
7-bromoimidazo[1,5-a]pyridine Preparation Products And Raw materials
Raw materialsN-((4-bromopyridin-2-yl)methyl)formamide-->Trifluoroacetic anhydride-->Dichloromethane
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