A method for catalytically converting cyano groups into deuterated methyl groups, prepared aromatic deuterated methyl compounds and applications thereof
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A catalytic conversion and compound technology, applied in the direction of hydrocarbons, hydrocarbons, organic chemical methods, etc., can solve the problems that cannot be applied to the synthesis of deuterated methyl groups, high temperature, etc., to achieve large-scale production and maintain basic Unchanged, high-yield effects
Active Publication Date: 2020-12-29
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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Synthesis, 1980, 10, 802-803 reported that under the pressure of hydrogen, nickel / alumina as a catalyst can directly convert cyano groups into methyl groups, but this method requires a very high temperature to achieve
There are also some methods for converting cyano groups into methyl groups, but the source of hydrogen does not originate from hydrogen. As Chem Ber, 99,227,1966 reported that cyano groups were directly converted into methyl groups under the catalysis of 10% Pd / C, but Its hydrogen source is a kind of iron compound, unless there is a deuterated iron compound as a deuterium source, otherwise such a method cannot be applied to the synthesis of deuterated methyl
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Embodiment 1
[0030] In this example, an aromatic deuterated methyl compound is prepared by the following preparation method, and the reaction formula is as follows:
[0031]
[0032] 2-Methoxybenzonitrile (1g) and deuterium-containing water palladium hydroxide on carbon (0.1g) were mixed in deuterated methanol (10mL), under 0.1MPa deuterium gas pressure, stirred at room temperature for 18 hours, after the reaction, 2-deuterated methyl anisole was obtained by filtration with a yield of 90% and a deuterated rate of 98%.
[0033] 1 H NMR (400MHz, d 6 -DMSO), δ7.15 (m, 2H), 6.92 (d, 1H), 6.84 (m, 1H), 3.77 (s, 3H); GC-MS: MS 125.
Embodiment 2
[0035] In this example, an aromatic deuterated methyl compound is prepared by the following preparation method, and the reaction formula is as follows:
[0036]
[0037] 2-Methoxybenzonitrile (1g) and anhydrous palladium carbon (0.1g) were mixed in deuterated methanol (10mL), under 0.1MPa deuterium gas pressure, stirred at room temperature for 48 hours, after the reaction was completed, filtered to obtain 2 - deuterated methyl anisole, yield 92%, deuterium rate 98.3%.
Embodiment 3
[0039] In this example, an aromatic deuterated methyl compound is prepared by the following preparation method, and the reaction formula is as follows:
[0040]
[0041] Mix 2-methoxybenzonitrile (1g) and anhydrous palladium carbon (0.1g) in deuterated methanol (10mL), under 0.1MPa deuterium gas pressure, stir at 60 degrees for 24 hours, after the reaction is completed, filter to obtain 2-Deuterated methyl anisole, the yield is 90%, and the deuterated rate is 98.2%.
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Abstract
The invention provides a method for catalytic conversion of a cyano group into deuterated methyl, a prepared aromatic deuterated methyl compound and an application of the compound. The method comprises the steps as follows: an aromatic cyano compound reacts to produce the aromatic deuterated methyl compound under the action of a metal catalyst with deuterium gas serving as a deuterium source. The cyano group is directly catalyzed into deuterated methyl with the deuterium gas serving as the deuterium source, the operation is simple, the raw material is cheap and easy to obtain, the reaction yield is high, the product deuteration rate is high, and the method can be applied to mass production. The prepared aromatic deuterated methyl compound can be used as a deuterated medicine or can be used for preparation of a deuterated medicine or deuterated medicine composition, and the pharmacokinetics, pharmacodynamics or metabolism toxicity of the medicine can be reduced while the medicine molecular activity is kept unchanged basically.
Description
technical field [0001] The invention belongs to the technical field of compound synthesis, and relates to a method for converting a cyano group into a deuterated methyl group through catalysis, an aromatic deuterated methyl compound prepared therefrom and an application thereof. Background technique [0002] Deuterium is a stable isotope of hydrogen, its relative atomic mass is twice that of hydrogen, and in general, deuterium has very low toxicity. Due to the nature of deuterium, the carbon-deuterium bond (C-D) in the compound has a lower vibrational zero-point energy than the carbon-hydrogen bond (C-H) and is more stable. Therefore, in drugs, part of the hydrogen atoms are replaced by deuterium atoms, so as to maintain the activity of the drug molecule basically unchanged, improve the pharmacokinetics and pharmacodynamics of the drug or reduce the metabolic toxicity of the drug. [0003] At present, the common deuterated drugs are to replace part of the methyl groups in t...
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