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Aminomethylated imidazo[1,2-a]pyridine compound and preparation method thereof

A technology for amine methylation of imidazole and 2-a, which is applied in the field of synthesis of amine alkylation of imidazo[1,2-a]pyridine compounds, achieving the effects of less by-products, mild reaction conditions and good chemoselectivity

Active Publication Date: 2019-04-19
EAST CHINA UNIV OF TECH
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

As far as we know, there are no patents or literature reports on the use of visible light to promote the decarboxylation coupling reaction of imidazo[1,2-a]pyridine compounds and α-amino acid compounds.

Method used

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  • Aminomethylated imidazo[1,2-a]pyridine compound and preparation method thereof
  • Aminomethylated imidazo[1,2-a]pyridine compound and preparation method thereof
  • Aminomethylated imidazo[1,2-a]pyridine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add N-4-tolylglycine (0.3mmol), 2-phenylimidazo[1,2-a]pyridine (0.2mmol) into a dry reaction tube with a stirring magnet. Then, toluene (2 mL) was added to the test tube as a solvent, and the reaction mixture was placed in an air atmosphere at 35° C. under LED blue light irradiation for 35 hours. After the reaction was detected by TLC, the solvent was distilled off with a rotary evaporator under reduced pressure, and the residue was separated and purified by column chromatography to obtain a pure light yellow solid 3aa with a yield of 82%. The structural characterization data of the 3aa compound are as follows:

[0021]

[0022] light yellow solid; mp 164.1-165.4°C; 1 H NMR (400MHz, CDCl 3 ): δ8.16(d, J=5.6Hz, 1H), 7.80(d, J=5.6Hz, 2H), 7.73(d, J=7.2Hz, 1H), 7.46(t, J=6.0Hz, 2H ),7.38(t,J=6.0Hz,1H),7.28(t,J=6.2Hz,1H),7.08(t,J=6.4Hz,2H),6.87(t,J=5.4Hz,1H), 6.69(d, J=6.8Hz, 2H), 4.70(s, 2H), 2.29(s, 3H); 13 C NMR (100MHz, CDCl 3 ): δ145.3, 145.2, 144.6, 133.9, 13...

Embodiment 2

[0024] Add N-4-tolylglycine (0.3mmol), 2-(4-tolyl)imidazo[1,2-a]pyridine (0.2mmol) into a dry reaction tube with a stirring magnet. Then, toluene (2 mL) was added to the test tube as a solvent, and the reaction mixture was placed in an air atmosphere at 35° C. under LED blue light irradiation for 40 hours. After the reaction was detected by TLC, the solvent was distilled off with a rotary evaporator under reduced pressure, and the residue was separated and purified by column chromatography to obtain a pure light yellow solid 3ab with a yield of 83%. The structural characterization data of the 3ab compound are as follows:

[0025]

[0026] light yellow solid; mp 151.4-152.6℃; 1 H NMR (400MHz, CDCl 3 ):δ8.07(d,J=5.6Hz,1H),7.64(d,J=8.0Hz,3H),7.25-7.19(m,3H),7.06(d,J=6.4Hz,2H),6.78 (dd, J=5.6Hz, J=1.0Hz, 1H), 6.67(d, J=6.8Hz, 2H), 4.63(s, 2H), 3.75(brs, 1H), 2.37(s, 3H), 2.28 (s,3H); 13 C NMR (100MHz, CDCl 3 ): δ145.4, 145.1, 144.6, 137.9, 131.0, 130.0, 129.5, 128.2, 127....

Embodiment 3

[0028] Add N-4-tolylglycine (0.3mmol), 2-(4-methoxyphenyl)imidazo[1,2-a]pyridine (0.2mmol) into a dry reaction tube with stirring magnet . Then, toluene (2 mL) was added to the test tube as a solvent, and the reaction mixture was placed in an air atmosphere at 35° C. under LED blue light irradiation for 30 hours. After the reaction was detected by TLC, the solvent was distilled off with a rotary evaporator under reduced pressure, and the residue was separated and purified by column chromatography to obtain a pure brown solid 3ac with a yield of 64%. The structural characterization data of the 3ac compound are as follows:

[0029]

[0030] light yellow solid; mp 174.3-175.5℃; 1H NMR (400MHz, CDCl 3 ): δ8.09(d, J=5.6Hz, 1H), 7.71(dd, J=5.6Hz, J=1.6Hz, 2H), 7.65(d, J=7.2Hz, 1H), 7.24-7.20(m ,1H),7.07(d,J=6.4Hz,2H),6.96(dt,J=7.2Hz,J=1.8Hz,2H),6.81(td,J=5.4Hz,J=0.8Hz,1H), 6.68(d, J=6.4Hz, 2H), 4.64(s, 2H), 3.83(s, 3H), 2.29(s, 3H); 13 C NMR (100MHz, CDCl 3 ): δ159.6, 145....

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Abstract

The invention discloses a synthesis method of an aminomethylated imidazo[1,2-a]pyridine compound; and according to the synthesis method, N-aryl glycine and imidazo[1,2-a]pyridine carry out decarboxylation coupling reactions in the presence of visible light. In an organic solvent, N-aryl glycine and imidazo[1,2-a]pyridine derivatives carry out reactions to prepare the aminomethylated imidazo[1,2-a]pyridine compound under the irradiation of visible light. The structure of the compound is tested and characterized by 1H NMR, 13C NMR, and HR-MS so as to determine the structure. The preparation method does not need any photo-sensitizer or additive, oxygen in the air is taken as the final oxidizing agent, and N-aryl glycine is induced by light to carry out decarboxylation, is oxidized, and reactswith imidazo[1,2-a]pyridine to prepare the aminomethylated imidazo[1,2-a]pyridine compound. The synthesis route is simple, convenient and efficient, the reaction conditions are middle, the operationis simple, and the synthesis method is environmentally friendly, can be applied to large scale production, and has a very good application prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to the synthesis of imidazo[1,2-a]pyridine derivatives, in particular to a synthesis method of visible light-promoted amine alkylation of imidazo[1,2-a]pyridine compounds. Background technique [0002] Photocatalysis has a series of advantages such as simple operation, environmental friendliness, green and clean, safe, convenient and sustainable. In recent years, visible light-induced photoredox construction of carbon-carbon and carbon-heteroatom bonds has developed into a very important class of organic synthesis methods. α-Amino acids are organic molecules that make up the basic structure of proteins and are ubiquitous in natural products, drug molecules and compounds with biological activity. Therefore, α-amino acid compounds are widely used in organic synthesis as a non-fossil fuel-friendly environment-friendly carbon source. Moreover, the promotion of decarboxylation of α-amino...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 祝志强季久健谢宗波乐长高
Owner EAST CHINA UNIV OF TECH
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