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.

Active Publication Date: 2017-08-25
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the research on the functionalization reaction of pyridoimidazole has become more and more mature, but there are few reports on the sulfonylmethylation reaction of pyridoimidazole

Method used

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  • 2-phenyl-3-(tosylmethyl)imidazo[1,2-a]pyridine compound and its synthesis method
  • 2-phenyl-3-(tosylmethyl)imidazo[1,2-a]pyridine compound and its synthesis method
  • 2-phenyl-3-(tosylmethyl)imidazo[1,2-a]pyridine compound and its synthesis method

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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,...

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Abstract

The invention discloses a 2-phenyl-3-(toluenesulfonylmethyl) imidazo[1,2-a] pyridine compound and a preparation method thereof. The preparation method comprises the following steps: adding 2-phenyl-imidazo [1,2-a] pyridine compound and p-tolylsulfonylmethyl isocyanide into a reaction tube in an argon environment, adding ferric trichloride, then adding a green solvent, and reacting for 18 to 48 hours at 80 to 120 DEG C; and after the reaction, extracting, chromatographically separating, and drying to obtain a target product. In the reaction, cheap metal ion (III) is used as a catalyst, water and polyethylene glycol 400 are used as reaction solvents, the sulfonylmethylation reaction of the imidazo [1,2-a] pyridine compound and p-tolylsulfonylmethyl isocyanide is realized, sulfonyl of the obtained compound is used as a leaving group, and the further functional group reaction is realized. The method has important significance on the research and application of the sulfonylmethylation reaction of the imidazo [1,2-a] pyridine compound.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis and application, and in particular relates to a preparation method of 2-phenyl-3-(tosylmethyl)imidazo[1,2-a]pyridine compounds. Background technique [0002] Pyridoimidazole is a very important and common nitrogen heterocyclic compound (ComprehensiveHeterocyclic Chemistry III). Its derivatives have good biological activity: for example, antiviral, antiulcer and antibacterial properties (J.Med.Chem.2015,58,8529; Bioorg.Med.Chem.Lett.2013,23,4996; J.Med. Chem. 2015, 58, 9238; Bioorg. Med. Chem. 2011, 19, 4227; ACS Med. Chem. Lett. 2013, 4, 675; J. Med. Chem. 1999, 42, 50). Among them, several types of drugs have been successfully marketed, such as anti-anxiety drugs Alpidem (Alpidem), Saripidem (Saripidem), anesthetics Necopidem (Necopidem) and sedative-hypnotics Zolpidem (Zolpidem), etc. ( J. Med. Chem. 2008, 51, 7243; Exp. Ther. 2001, 299, 793; J. Behav. Pharmacol. 1995, 6, 11...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 朱新举卢帅杨发琉郭玉静田子瑶郝新奇赵雪梅宋毛平
Owner ZHENGZHOU UNIV
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