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4-chloroindole compound and preparation method thereof
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A technology of indole compound and chloroindole, applied in the direction of organic chemistry, etc., can solve the problems of explosion, difficulty in large-scale application, fire, etc., and achieve the effects of high product purity, less side reactions and good application prospects.
Active Publication Date: 2020-12-04
PINGDINGSHAN UNIVERSITY +1
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Problems solved by technology
As we all know, metalthallium (Tl) and mercury (Hg) are both highly toxic heavy metals, and tert-butyllithium is very active. Once it is improperly handled, it will react violently when it encounters air, causing fire or even explosion. Known methods have insurmountable defects and limitations, making it difficult to apply them on a large scale in actual production
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Embodiment 1
[0054] Add N-benzoylindole-3-carbaldehyde (0.2mmol), N-chlorosuccinimide (0.24mmol), catalyst palladium acetate (10mol%), temporary directing group 2 respectively in the reaction test tube successively. - Amino-4-nitrobenzoic acid (45 mol%), acid additive trifluoroacetic acid (10.0 equiv), and finally the solventchlorobenzene (1 mL), and the reaction tube was sealed with a rubber stopper. Place the test tube in an oil bath at 50°C and heat it with stirring for about 24 hours. During the reaction, TLC is used to detect that the reaction is complete. During the post-treatment, the solvent was spin-dried first, and the pure product N-benzoyl-4-chloroindole-3-carbaldehyde compound 3a was directly separated by silica gelcolumn chromatography.
[0055]
[0056] Compound 3a, yield: 85%; white solid; melting point 125-127°C; 1 H NMR (400MHz, CDCl 3 )δ10.79(s,1H),8.36(d,J=8.0Hz,1H),8.08(s,1H),7.76–7.74(m,2H),7.69(t,J=7.6Hz,1H), 7.58(t, J=7.6Hz, 2H), 7.44(d, J=7.2Hz, 1H), 7.38(t...
Embodiment 2
[0059] The reactants are N-acetylindole-3-carbaldehyde and N-chlorosuccinimide, and the product is N-acetyl-4-chloroindole-3-carbaldehyde compound 3b.
[0063] The reactants are N-benzyloxycarbonyl indole-3-carbaldehyde and N-chlorosuccinimide, and the product is N-benzyloxycarbonyl-4-chloroindole-3-carbaldehyde compound 3c.
[0064]
[0065] N-benzyloxycarbonyl-4-chloroindole-3-carbaldehyde compound 3c, yield: 46%; white solid; melting point 93-95°C; 1 HNMR (400MHz, CDCl 3 )δ10.78(s,1H),8.42(s,1H),8.23(d,J=8.0Hz,1H),7.50–7.43(m,5H),7.39(d,J=8.0Hz,1H), 7.33(t,J=8.0Hz,1H),5.49(s,2H); 13 C NMR (100MHz, CDCl 3 )δ186.9,149.8,137.2,134.0,131.2,129.3,129.0,128.9,126.3,126.2,125.4,125.1,121.8,114.3,70.1; HRMS(pos.ESI):m / z[M+H] + for C 17 h 13 ClNO 3 calcd: 314.0578, found: 314.0624.
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Abstract
The invention discloses a 4-chloroindole compound and a preparation method thereof. The 4-chloroindole compound is prepared by taking various N-protected indolo-3-formaldehyde and N-chlorosuccinimide(NCS) as reaction substrates. The structural formula of the 4-chloroindole compound is shown in the specification. The reaction yield can reach medium to excellent, the chemical selectivity and regioselectivity of the reaction are excellent, the reaction conditions are mild, and the application range of a substrate is wide,the method has the advantages of simple operation, low cost, few side reactions, high product purity, convenient separation and purification, and suitableness for large-scale preparation, so the obtained product has a very good application prospect in the field of biologicalmedicines.
Description
technical field [0001] The invention relates to a heterocyclic compound and a preparation method thereof, in particular to a 4-position chloroindole compound and a preparation method thereof. Background technique [0002] Nitrogen-containing heterocyclic compounds are common core structures of natural products and many drug molecules. Indole, which has a special structure of benzopyrrole, is an important class of natural nitrogen-containing alkaloid compounds. Indole heterocyclic compounds often have a broad spectrum of physiological and pharmaceutical activities, so the rapid and efficient synthesis of indole compounds and their diverse modifications have always attracted the research interests of organic chemists and medicinal chemists ((a) N.K.Kaushik , N. Kaushik, P. Attri, N. Kumar, C.H. Kim, A.K. Verma, E.H. Choi, Molecules, 2013, 18, 6620-6662; (b) H. Patel, N. Darji, J. Pillai, B. Patel , Int.J.Drug Res.Tech.2012,2,225; (c)S.Biswal,U.Sahoo,S.Sethy,H.K.S.Kumar,M.Bane...
Claims
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Application Information
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