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Difluoromethylation synthesis method of aromatic amine compound
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A technology of aromatic amines and difluoromethyl, which is applied in the field of difluoromethylation synthesis of aromatic amine compounds, can solve the problems of harsh reaction conditions, poor functional group compatibility, long reaction time, etc., and achieve short reaction time and excellent conditions Gentle, easy-to-apply results
Active Publication Date: 2019-12-31
SHANGHAI INST OF TECH
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[0002] Due to the widespread existence of hydrogen bonds in biological systems and their indispensable role in realizing various physiological functions, in medicinal chemistry, the use of difluoromethyl (-CF 2 H) As a structural mimic of amino groups in bioactive molecules, it has also attracted considerable attention. The traditional methods for introducing difluoromethyl groups on amino groups usually have harsh reaction conditions, long reaction times, and poor functional group compatibility.
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Embodiment 1
[0026] Preparation of 1-(difluoromethyl)-1H-benzo[d]imidazole
[0027]
[0028] Weigh 1H-benzo[d]imidazole (118mg 1mmol) and place it in a 10mL round bottom flask, then add 2,2-difluoro-2-iodo-1-phenylethan-1-one (564mg 1mmol), On a magnetic stirrer, react for 15 minutes, TLC monitors that the reaction is complete; spin dry, add water, extract with ethyl acetate 3 times, concentrate, and chromatographically separate (PE:EA (v / v)=2:1) to obtain a light yellow oil (Yield 77%).
[0029] analyzed by the 1 H NMR (500MHz, CDCl 3 ):8.13(s,1H), 7.86-7.82(m,1H), 7.62-7.59(m,1H), 7.42-7.36(m,2H), 7.33(t,J=60.30Hz,1H); ESI- HRMS(m / z): calculated for C 8 h 6 f 2 N 2 (M+H) + :168.0543.2839,found:168.0547.
Embodiment 2
[0031] Preparation of 5-bromo-1-(difluoromethyl)-1H-indazole
[0032]
[0033] The difference from Example 1 is that the aniline compound used is 5-bromo-1H-indazole, and other reaction conditions and steps are the same as in Example 1, reacting at room temperature for 15 minutes, and a light yellow oily substance is obtained after one cycle (Yield 69%).
[0034] analyzed by the 1 H NMR (500MHz, CDCl 3 ):8.27(s,1H), 7.84(d,J=1Hz,1H), 7.60(d,J=9.25Hz,1H), 7.44(t,J=60.48Hz,1H), 7.39(dd,J= 9.2Hz,1H); ESI-HRMS(m / z): calculated for C 8 h 5 BrF 2 N 2 (M+H) + :245.9633,found:245.9638.
Embodiment 3
[0036] Preparation of 1-(1-(difluoromethyl)-1H-indol-3-yl)ethan-1-one
[0037]
[0038] The difference from Example 1 is that the aniline compound used is 5-bromo-1H-indazole, and other reaction conditions and steps are the same as in Example 1, reacting at room temperature for 15 minutes, and a light yellow oily substance is obtained after one cycle (Yield 81%).
[0039] analyzed by the 1 H NMR (500MHz, CDCl 3 ):8.42-8.36(m,1H), 7.92(s,1H), 7.56-7.52(m,1H), 7.39-7.34(m,2H), 7.33(t,J=60.68Hz,1H); ESI- HRMS(m / z): calculated for C 11 h 9 f 2 NO(M+H) + :209.0718,found:209.0714.
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Abstract
The invention relates to a difluoromethylation synthesis method of an aromatic amine compound, wherein an amine compound and a difluoroiodo ketone compound are used as raw materials, and are subjectedto a reaction at a room temperature by using acetonitrile and water as solvents, the reaction is tracked by thin layerchromatography until the reaction is completed, and post-treatment is performedto obtain a difluoromethyl-containing compound. According to the invention, the synthetic method is provided, and is mild in reaction condition and short in reaction time, and the prepared compound can be used for synthesizing medicines in the field of medicines and pesticides.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a difluoromethylation synthesis method of aromatic amine compounds. Background technique [0002] Due to the widespread existence of hydrogen bonds in biological systems and their indispensable role in realizing various physiological functions, in medicinal chemistry, the use of difluoromethyl (-CF 2 H) As a structural mimic of amino groups in bioactive molecules, it has also attracted considerable attention. Traditional methods for introducing difluoromethyl groups on amino groups usually have harsh reaction conditions, long reaction times, and poor functional group compatibility. [0003] In recent years, fluorine-containing drugs account for a large proportion of clinical therapeutic drugs. The introduction of fluorine atoms or fluorine-containing groups into small molecule drugs is one of the important strategies to improve drug activity. The introduction of fluori...
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