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N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline compound and its synthesis method

A technology of aniline compounds and phenylimidazole, which is applied in the field of organic compound synthesis and application, 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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  • 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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  • N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline compound and its synthesis method
  • N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline compound and its synthesis method
  • N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline compound and its synthesis method

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Experimental program
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Embodiment 1

[0024] The structural formula of the compound N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline of this embodiment is:

[0025]

[0026] The preparation method is: in an air environment, add 0.1mmol of 2-phenylimidazo[1,2-a]pyridine compound, 0.3mmol of aniline, 0.2mmol of di-tert-butyl peroxide into a 35mL high-pressure tube, 0.1mmol of potassium permanganate, 0.2mmol of sodium tert-butoxide, 2mL of hexafluoroisopropanol and methanol (volume ratio 1:9), react at 100°C for 12 hours; after the reaction, chromatographic separation (silica gel 200-300 mesh, Eluent: gradient elution with ethyl acetate / petroleum ether (ratio from 0 / 100 to 100 / 0), drying to obtain a light yellow solid with a yield of 50%. mp 191-192°C; 1 H NMR (600MHz, DMSO) δ8.34 (d, J = 6.8Hz, 1H), 7.81 (d, J = 7.7Hz, 2H), 7.64 (d, J = 9.0Hz, 1H), 7.48 (t, J =7.5Hz, 2H), 7.38(t, J=7.3Hz, 1H), 7.34–7.26(m, 1H), 7.08(t, J=7.5Hz, 2H), 6.97(t, J=6.7Hz, 1H ), 6.66(d, J=7.9Hz, 2H), 6.59(t, J=7.2Hz, 1H), 6.15(t...

Embodiment 2

[0028] The structural formula of the compound N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline of this embodiment is:

[0029]

[0030] The preparation method is: in an air environment, add 0.1mmol of 2-phenylimidazo[1,2-a]pyridine compound, 0.3mmol of aniline, 0.1mmol of di-tert-butyl peroxide into a 35mL high-pressure tube, 0.2mmol of potassium permanganate, 0.1mmol of sodium tert-butoxide, 2mL of hexafluoroisopropanol and methanol (volume ratio 1:9), react at 140°C for 10 hours; after the reaction, chromatographic separation (silica gel 200-300 mesh, Eluent: gradient elution with ethyl acetate / petroleum ether (ratio from 0 / 100 to 100 / 0), drying to obtain a light yellow solid with a yield of 62%. mp 191-192°C; 1 H NMR (600MHz, DMSO) δ8.34 (d, J = 6.8Hz, 1H), 7.81 (d, J = 7.7Hz, 2H), 7.64 (d, J = 9.0Hz, 1H), 7.48 (t, J =7.5Hz, 2H), 7.38(t, J=7.3Hz, 1H), 7.34–7.26(m, 1H), 7.08(t, J=7.5Hz, 2H), 6.97(t, J=6.7Hz, 1H ), 6.66(d, J=7.9Hz, 2H), 6.59(t, J=7.2Hz, 1H), 6.15(t...

Embodiment 3

[0032] The structural formula of the compound N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline of this embodiment is:

[0033]

[0034]The preparation method is: in an air environment, add 0.1mmol of 2-phenylimidazo[1,2-a]pyridine compound, 0.2mmol of aniline, 0.2mmol of di-tert-butyl peroxide into a 35mL high-pressure tube, 0.1mmol of potassium permanganate, 0.1mmol of sodium tert-butoxide, 2mL of hexafluoroisopropanol and methanol (volume ratio 1:9), react at 130°C for 8 hours; after the reaction, chromatographic separation (silica gel 200-300 mesh, Eluent: gradient elution with ethyl acetate / petroleum ether (ratio from 0 / 100 to 100 / 0), drying to obtain a light yellow solid with a yield of 62%. mp 191-192°C; 1 H NMR (600MHz, DMSO) δ8.34 (d, J = 6.8Hz, 1H), 7.81 (d, J = 7.7Hz, 2H), 7.64 (d, J = 9.0Hz, 1H), 7.48 (t, J =7.5Hz, 2H), 7.38(t, J=7.3Hz, 1H), 7.34–7.26(m, 1H), 7.08(t, J=7.5Hz, 2H), 6.97(t, J=6.7Hz, 1H ), 6.66(d, J=7.9Hz, 2H), 6.59(t, J=7.2Hz, 1H), 6.15(t, ...

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Abstract

The invention discloses an N-((2-phenyl imidazo[1,2-a]pyridine-3-yl)methyl)phenylamine compound and a synthesis method thereof. The synthesis method includes the following steps that in an air environment, 2-phenyl-imidazo[1,2-a]pyridine and a phenylamine compound are added into a reaction tube, di-tert-butyl peroxide, potassium permanganate, sodium tert-butoxide and solvents are sequentially added, and reaction is conducted for 8-12 hours at 100-140 DEG C; and after the reaction is completed, a target product is obtained through chromatographic separation and drying. According to the reaction, methanol and hexafluoroisopropanol are used as the reaction solvents, so that amino methylation of the imidazo[1,2-a]pyridine compound and phenylamine is achieved, the method is simple and efficient, the cost is low, purification is easy, substrate adaptability is wide, and functionalization reaction types of the imidazo[1,2-a]pyridine compound are enriched; the method has important significancefor research and application of amino methylation 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 specifically relates to an N-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline compound and a synthesis method thereof. 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 i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
Inventor 徐琰张宁黄恩玲魏静娜王栩琰朱新举郝新奇宋毛平
Owner ZHENGZHOU UNIV
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