2-phenyl-3-(tosylmethyl)imidazo[1,2-a]pyridine compound and its synthesis method
A technology of toluenesulfonylmethyl and p-toluenesulfonylmethylisocyanide, which is applied in the field of organic compound synthesis and application, and can solve the problems that there are few reports on pyridoimidazole sulfonylmethylation.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0024] The structural formula of the compound 2-phenyl-3-(tosylmethyl)imidazo[1,2-a]pyridine of this embodiment is:
[0025]
[0026] The preparation method is: under the protection of argon, add 0.1mmol of 2-phenylimidazo[1,2-a]pyridine compound, 0.2mmol of p-toluenesulfonylmethyl isocyanide, 0.02 Mmol of ferric chloride, water and polyethylene glycol 400 (volume ratio 1:1) 2mL, react at 90°C for 24 hours; after the reaction, extract with dichloromethane, concentrate under reduced pressure and then chromatograph Mesh, eluent: gradient elution with ethyl acetate / petroleum ether, the ratio is from 0 / 100 to 100 / 0), and dried to obtain a white solid with a yield of 94%. m.p.=68-69°C. 1 H NMR (600MHz, CDCl 3 )δ8.45(d, J=6.8Hz, 1H), 7.67(d, J=8.9Hz, 1H), 7.38(d, J=8.1Hz, 2H), 7.33-7.27(m, 6H), 7.09( d, J=8.0Hz, 2H), 6.94(t, J=6.7Hz, 1H), 4.87(s, 2H), 2.36(s, 3H). 13 C NMR (150MHz, CDCl 3 )δ147.5, 146.0, 145.3, 134.2, 133.0, 129.8, 128.3, 128.22, 128.16, 128.1, 126.0, 124.9,...
Embodiment 2
[0028] The structural formula of the compound 2-(o-tolyl)-3-(tosylmethyl)imidazo[1,2-a]pyridine in this embodiment is:
[0029]
[0030] The preparation method is: add 0.1mmol of 2-o-tolyl imidazo[1,2-a]pyridine compound, 0.3mmol of p-toluenesulfonylmethyl isocyanide to a 10mL Shrek tube under the protection of argon, 0.03mmol of ferric chloride, 2mL of water, react at 110°C for 22 hours; after the reaction, extract with dichloromethane, concentrate under reduced pressure and then chromatographically separate (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether Gradient elution, the ratio is from 0 / 100 to 100 / 0), and dried to obtain a white solid with a yield of 89%. m.p.=133-134°C. 1 H NMR (600MHz, CDCl 3 )δ8.53(d, J=7.5Hz, 1H), 7.63(d, J=9Hz, 1H), 7.33-7.29(m, 3H), 7.21(t, J=7.5Hz, 1H), 7.13(d ,J=8.3Hz,1H),7.11(d,J=7.9Hz,2H),7.02(t,J=7.4Hz,1H),6.95(td,J=6.8,0.8Hz,1H),6.69(d ,J=7.0Hz,1H),4.72(s,2H),2.40(s,3H),1.99(s,3H). 13 C NMR (150MHz, CDCl 3 )δ147.9, 1...
Embodiment 3
[0032] The structural formula of the compound 2-(3-methoxyphenyl)-3-(tosylmethyl)imidazo[1,2-a]pyridine in this embodiment is:
[0033]
[0034] The preparation method is: add 0.1mmol of 2-(3-methoxyphenyl)imidazo[1,2-a]pyridine compound, 0.3mmol of p-toluenesulfonate to a 10mL Shrek tube under the protection of argon Acylmethylisonitrile, 0.02mmol of ferric chloride, water and polyethylene glycol 400 (volume ratio 2:1) 2mL, reacted at 100°C for 36 hours; after the reaction, extracted with dichloromethane, concentrated under reduced pressure Chromatographic separation (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0 / 100 to 100 / 0), dried to obtain a white solid with a yield of 98%. m.p.=173-174°C. 1 H NMR (600MHz, CDCl 3 )δ8.42(d, J=6.8Hz, 1H), 7.65(d, J=9.0Hz, 1H), 7.40(d, J=8.2Hz, 2H), 7.31-7.29(m, 1H), 7.19( t, J=7.9Hz, 1H), 7.10(d, J=8.1Hz, 2H), 6.96(s, 1H), 6.93-6.89(m, 2H), 6.84(dd, J=8.2, 2.2Hz, 1H ),4.88(s,2H),3.82(s,...
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