Synthesis of n-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamides

A technology of benzenesulfonamide and phenylimidazole, which is applied in the field of synthesis of N-methyl)benzenesulfonamide compounds, can solve few problems and achieve the effect of wide applicability of substrates

Active Publication Date: 2020-07-17
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the use of methanol as the methylene synthesis moiety for C–H aminomethylation has been rarely reported

Method used

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  • Synthesis of n-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamides
  • Synthesis of n-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamides
  • Synthesis of n-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamides

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The structural formula of the compound N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamide of the present embodiment is:

[0026]

[0027] The preparation method is: in an air environment, add 0.1mmol of 2-phenylimidazo[1,2-a]pyridine compound, 0.2mmol of benzenesulfonamide, and 0.1mmol of di-tert-butyl peroxide into a 35mL high-pressure tube 0.2 mmol of potassium permanganate, 0.1 mmol of sodium tert-butoxide, 2 mL of hexafluoroisopropanol and methanol (volume ratio 1:1), reacted at 100 ° C for 12 hours; after the reaction, chromatographic separation (silica gel 200-300 Mesh, eluent: gradient elution with ethyl acetate / petroleum ether, the ratio is from 0 / 100 to 100 / 0), and dried to obtain a yellow solid with a yield of 78%. m.p.=208-209℃. 1 H NMR (600MHz, DMSO) δ8.29–8.25(m,2H),7.79(d,J=7.0Hz,2H),7.64(d,J=4.7Hz,3H),7.60–7.56(m,3H) ,7.42–7.28(m,4H),7.00(t,J=5.5Hz,1H),4.46(s,2H); 13 C NMR (101MHz, DMSO) δ144.2, 143.7, 139.5, 133.9, 132.6, 129.1, 128.4...

Embodiment 2

[0029] The structural formula of the compound N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamide of the present embodiment is:

[0030]

[0031] The preparation method is: in an air environment, add 0.1mmol of 2-phenylimidazo[1,2-a]pyridine compound, 0.2mmol of benzenesulfonamide, 0.2mmol of di-tert-butyl peroxide into a 35mL high-pressure tube 0.1 mmol of potassium permanganate, 0.1 mmol of sodium tert-butoxide, 2 mL of hexafluoroisopropanol and methanol (volume ratio 1:9), reacted at 130 ° C for 8 hours; after the reaction, chromatographic separation (silica gel 200-300 Mesh, eluent: gradient elution with ethyl acetate / petroleum ether, the ratio is from 0 / 100 to 100 / 0), and dried to obtain a yellow solid with a yield of 85%. m.p.=208-209℃. 1 H NMR (600MHz, DMSO) δ8.29–8.25(m,2H),7.79(d,J=7.0Hz,2H),7.64(d,J=4.7Hz,3H),7.60–7.56(m,3H) ,7.42–7.28(m,4H),7.00(t,J=5.5Hz,1H),4.46(s,2H); 13 C NMR (101MHz, DMSO) δ144.2, 143.7, 139.5, 133.9, 132.6, 129.1, 128.4, 128...

Embodiment 3

[0033] The structural formula of the compound N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamide of the present embodiment is:

[0034]

[0035]The preparation method is: in an air environment, add 0.1mmol of 2-phenylimidazo[1,2-a]pyridine compound, 0.3mmol of benzenesulfonamide, 0.3mmol of di-tert-butyl peroxide into a 35mL high-pressure tube 0.1 mmol of potassium permanganate, 0.2 mmol of sodium tert-butoxide, 2 mL of hexafluoroisopropanol and methanol (volume ratio 1:9), reacted at 100 ° C for 12 hours; after the reaction, chromatographic separation (silica gel 200-300 Mesh, eluent: gradient elution with ethyl acetate / petroleum ether, the ratio is from 0 / 100 to 100 / 0), and dried to obtain a yellow solid with a yield of 75%. m.p.=208-209℃. 1 H NMR (600MHz, DMSO) δ8.29–8.25(m,2H),7.79(d,J=7.0Hz,2H),7.64(d,J=4.7Hz,3H),7.60–7.56(m,3H) ,7.42–7.28(m,4H),7.00(t,J=5.5Hz,1H),4.46(s,2H); 13 C NMR (101MHz, DMSO) δ144.2, 143.7, 139.5, 133.9, 132.6, 129.1, 128.4, 128...

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Abstract

The invention discloses an N-((2-phenylimidazo [1,2-a] pyridine-3-yl) methyl) benzenesulfonamide compound and a synthesis method thereof. The method includes the following steps: adding a 2-phenyl-imidazo [1,2-a] pyridine compound and benzenesulfonamide into a reaction tube in an air environment, adding di-tert-butyl peroxide, potassium permanganate and sodium tert-butoxide, then adding a solvent,and reacting for 8-12 hours at 100-140 DEG C; and preforming chromatographic separation and drying after the reaction is completed to obtain a target product. Methanol and hexafluoroisopropanol are taken as reaction solvents in the reaction to realize a sulfonamide methylation reaction of an imidazo [1,2-a] pyridine compound and benzenesulfonamide; and the method is simple and efficient, low in cost and easy to purify, has wide base material applicability, enriches functionalization reaction types of the imidazo [1,2-a] pyridine compound, and further realizes a new reaction mode of the benzenesulfonamide.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis and application, and in particular relates to a synthesis method of N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamide compounds. Background technique [0002] As a special N-heterocycle, imidazo[1,2-a]pyridine has various biological activities (Med. Chem. 2007, 7, 888-899; Med. Chem. 2016, 16, 2963-2994.). Various commercialized drugs such as albatide, zolpidem, GSK812397, minodronic acid, nedopiperidine, and thalidomide have been prepared by appropriately inserting amidomethyl, hydroxymethyl, or other groups at the C3 position Degree, for the treatment of insomnia, anxiety, HIV infection and osteoporosis. In recent years, the research on the functionalization reaction of pyridoimidazole has become more and more mature, but there are few reports on the sulfonamide methylation reaction of imidazo[1,2-a]pyridine. Considering the importance of methylene-containing ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
Inventor 赵雪梅王梦玲魏静娜颜花婷黄恩玲朱新举郝新奇宋毛平
Owner ZHENGZHOU UNIV
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