| Identification | Back Directory | [Name]
7-bromoimidazo[1,5-a]pyridine | [CAS]
865156-48-5 | [Synonyms]
7-bromoimidazo[1,5-a]pyridine
Imidazo[1,5-a]pyridine, 7-bromo- | [Molecular Formula]
C7H5BrN2 | [MDL Number]
MFCD18074240 | [MOL File]
865156-48-5.mol | [Molecular Weight]
197.03 |
| Chemical Properties | Back Directory | [density ]
1.69±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
6.02±0.30(Predicted) | [Appearance]
Yellow to brown Solid | [CAS DataBase Reference]
865156-48-5 |
| Hazard Information | Back Directory | [Uses]
7-Bromoimidazo[1,5-a]pyridine is used in the discovery of novel imidazopyridine GSK-3β inhibitors supported by computational approaches. | [Synthesis]
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 |
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