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2-phenyl-3-(benzenesulfonyl)imidazo[1,2-a]pyridine compound and synthetic method thereof

A technology of benzenesulfonyl and imidazolium, which is applied in the field of organic compound synthesis and application, can solve the problems of few research reports on pyridoimidazole sulfonylation reaction and the like

Inactive Publication Date: 2018-02-06
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 sulfonylation reaction of pyridoimidazole

Method used

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  • 2-phenyl-3-(benzenesulfonyl)imidazo[1,2-a]pyridine compound and synthetic method thereof
  • 2-phenyl-3-(benzenesulfonyl)imidazo[1,2-a]pyridine compound and synthetic method thereof
  • 2-phenyl-3-(benzenesulfonyl)imidazo[1,2-a]pyridine compound and synthetic method thereof

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Experimental program
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Embodiment 1

[0021] The structural formula of the compound 2-p-fluorophenyl-3-(benzenesulfonyl)imidazo[1,2-a]pyridine in this embodiment is:

[0022] The preparation method is: in an air environment, add 0.2mmol of 2-p-fluorophenylimidazo[1,2-a]pyridine compound, 0.6mmol of sodium benzenesulfinate, and 0.3mmol of iodine into a 15mL high-pressure tube , 0.3 mmol of sodium carbonate, 2 mL of diethyl ether, and reacted at 100°C for 24 hours; / 100 to 100 / 0), and dried to obtain a white solid with a yield of 92%. m.p.=116-117°C. 1 H NMR (400MHz, CDCl 3 )δ9.11(d,t,J=7.0MHz,J=1.0MHz 1H),7.78-7.70(m,3H),7.65-7.63(m,2H),7.51-7.44(m,2H),7.39- 7.34(m,2H),7.18-7.13(m,2H),7.09-7.05(m,1H). 13 C NMR (600MHz, CDCl 3 ( d,J=39.3MHz).HRMS(positive ESI,m / z):[M+H] + calcd for C 19 h 14 FN 2 o 2 S + 353.0755,found 353.0755.

Embodiment 2

[0024] The structural formula of the compound 2-(3-chlorophenyl)-3-(benzenesulfonyl)imidazo[1,2-a]pyridine in this embodiment is:

[0025] The preparation method is: in an air environment, add 0.2mmol of 2-(3-chlorophenyl)imidazo[1,2-a]pyridine compound, 0.6mmol of sodium benzenesulfinate, 0.3mmol of elemental iodine, 0.3 mmol of sodium carbonate, 2 mL of diethyl ether, and reacted at 100°C for 24 hours; The ratio is from 0 / 100 to 100 / 0), and dried to obtain a white solid with a yield of 67%. m.p.=106-107°C. 1 H NMR (400MHz, CDCl 3 )δ9.12(d,t,J=7.0MHz,J=1.2MHz,1H),7.73-7.66(m,5H),7.53-7.43(m,3H),7.41-7.37(m,3H),7.09 (t,d,J=7.0Hz,J=1.3Hz,1H). 13 C NMR (600MHz, CDCl 3 )δ151.3, 146.7, 141.7, 134.4, 133.7, 133.6, 130.3, 129.4, 129.2, 129.1, 128.9, 126.8, 126.4, 118.1, 117.8, 114.9. HRMS (positive ESI): [M+H] + calcd for C 19 h 14 ClN 2 o 2 S + 369.0459, found 369.0468.

Embodiment 3

[0027] The structural formula of the compound 6-trifluoromethyl-2-phenyl-3-(benzenesulfonyl)imidazo[1,2-a]pyridine in this embodiment is:

[0028]

[0029]The preparation method is: add 0.2mmol of 6-trifluoromethyl-2-phenylimidazo[1,2-a]pyridine compound, 0.6mmol of sodium benzenesulfinate to a 15mL high-pressure tube under air environment, 0.3mmol of iodine, 0.3mmol of sodium carbonate, 2mL of diethyl ether, and react at 100°C for 24 hours; washed, the ratio is from 0 / 100 to 100 / 0), and dried to obtain a white solid with a yield of 72%. m.p.=145-146°C. 1 H NMR (400MHz, CDCl 3 )δ9.58(s,1H),7.82(d,J=9.4MHz,1H),7.73-7.70(m,2H),7.63-7.59(m,3H),7.50-7.45(m,4H),7.37 -7.33(m,2H). 13 C NMR (600MHz, CDCl 3 )δ154.3, 146.4, 141.4, 133.8, 131.8, 130.5, 129.8, 129.2, 128.0, 126.5, 126.0 (q, J = 22.7MHz), 124.4 (d, J = 8.0MHz), 124.0, 122.2, 119.3, 119.1, 118.8 ,118.7.HRMS(positive ESI):[M+H] + calcd for C 20 h 14 f 3 N 2 o 2 S + :403.0723, found 403.0724.

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Abstract

The invention discloses a 2-phenyl-3-(benzenesulfonyl)imidazo[1,2-a]pyridine compound and a synthetic method thereof. The synthetic method comprises the following steps: adding a 2-phenyl-imidazo[1,2-a]pyridine compound and sodium benzenesulfinate into a high-pressure tube in an air environment, adding an iodine elementary substance and sodium carbonate, then adding an ethyl ether solvent, and reacting at the temperature of 100 DEG C for 24 to 48 hours; after the reaction, performing chromatographic separation and drying to obtain a target product. In the reaction, the inexpensive elemental iodine is taken as a catalyst, and ethyl ether is taken as a reaction solvent, so that sulfonylation reaction of the imidazo[1,2-a]pyridine compound and the sodium benzenesulfinate is realized, a sulfonyl group of the obtained compound can be taken as a leaving group, and further functionalization reaction is realized. The method has important significance to the research and application of the sulfonylation reaction of the imidazo[1,2-a]pyridine compound.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic compounds, and in particular relates to a preparation method of 2-phenyl-3-(benzenesulfonyl)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. 19...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 邵田郭玉静卢帅高翔曹筱妞朱新举郝新奇宋毛平
Owner ZHENGZHOU UNIV
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