Novel method for synthesizing cyano-substituted imidazo[1,5-a]pyridine
A cyano-substituted, 5-a technology is applied in the field of cyano-substituted imidazo[1,5-a]pyridine synthesis, and achieves the effects of simple operation and low cost
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0021] Example 1: Synthesis of 1-cyano-3-phenylimidazo[1,5-a]pyridine
[0022] In a dry reactor, add NH 4 SCN (0.6 mmol, 46 mg), pyridine-2-carbaldehyde (0.3 mmol) and benzylamine (0.6 mmol) were then added to dimethylsulfoxide (2 mL). After stirring the mixture at room temperature for 5 min, add I 2 o 5 (0.3 mmol, 100 mg), and the mixture was further stirred at 100 °C for 5 h. After the reaction (TLC) was complete, the reaction mixture was cooled to room temperature and washed with saturated Na 2 S 2 o 3 The solution was quenched. The reaction mixture was then extracted with ethyl acetate. The organic phase was anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure to obtain a crude residue. Finally, the organic phase was concentrated on a rotary evaporator. The crude product was purified by column chromatography to obtain 1-cyano-3-phenylimidazo[1,5-a]pyridine. Yield: 95%.
[0023]
[0024] Structural Characterization Data: 1 H NMR (400MHz, Chlorofor...
Embodiment 2
[0025] Example 2: Synthesis of 1-cyano-3-phenylimidazo[1,5-a]pyridine
[0026] In a dry reactor, add NH 4 SCN (0.6mmol, 46mg), pyridine-2-carbaldehyde (0.3mmol) and benzylamine (0.45mmol) were added followed by dimethylsulfoxide (2mL). After stirring the mixture at room temperature for 5 min, add I 2 o 5(0.3 mmol, 100 mg), and the mixture was further stirred at 100 °C for 5 h. After the reaction (TLC) was complete, the reaction mixture was cooled to room temperature and washed with saturated Na 2 S 2 o 3 The solution was quenched. The reaction mixture was then extracted with ethyl acetate. The organic phase was anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure to obtain a crude residue. Finally, the organic phase was concentrated on a rotary evaporator. The crude product was purified by column chromatography to obtain 1-cyano-3-phenylimidazo[1,5-a]pyridine. Yield: 73%.
[0027]
[0028] Structural Characterization Data: 1 H NMR (400MHz, Chloroform...
Embodiment 3
[0029] Example 3: Synthesis of 1-cyano-3-phenylimidazo[1,5-a]pyridine
[0030] In a dry reactor, add NH 4 SCN (0.45 mmol, 35 mg), pyridine-2-carbaldehyde (0.3 mmol) and benzylamine (0.6 mmol) were then added to dimethylsulfoxide (2 mL). After stirring the mixture at room temperature for 5 min, add I 2 o 5 (0.3 mmol, 100 mg), and the mixture was further stirred at 100 °C for 5 h. After the reaction (TLC) was complete, the reaction mixture was cooled to room temperature and washed with saturated Na 2 S 2 o 3 The solution was quenched. The reaction mixture was then extracted with ethyl acetate. The organic phase was anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure to obtain a crude residue. Finally, the organic phase was concentrated on a rotary evaporator. The crude product was purified by column chromatography to obtain 1-cyano-3-phenylimidazo[1,5-a]pyridine. Yield: 69%.
[0031]
[0032] Structural Characterization Data: 1 H NMR (400MHz, Chlorofo...
PUM
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com