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4-position chloroindole compound and its preparation method

An indole compound and compound technology, applied in the direction of organic chemistry, can solve problems such as fire, explosion, and difficulty in large-scale application, and achieve the effects of high product purity, good application prospects, and less side reactions

Active Publication Date: 2022-03-22
PINGDINGSHAN UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As we all know, metal thallium (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

Method used

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  • 4-position chloroindole compound and its preparation method
  • 4-position chloroindole compound and its preparation method
  • 4-position chloroindole compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

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 solvent chlorobenzene (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 gel column 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.

[0060]

[0061] N-acetyl-4-chloroindole-3-carbaldehyde compound 3b, yield: 80%; white solid; melting point 170-171°C; 1 HNMR (400MHz, CDCl 3 )δ10.79(s,1H),8.43(d,J=8.0Hz,1H),8.21(s,1H),7.39(d,J=8.0Hz,1H),7.33(t,J=8.0Hz, 1H), 2.73(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ187.1, 168.9, 137.4, 130.5, 126.7, 126.0, 125.9, 125.0, 122.2, 115.6, 23.8; HRMS(pos.ESI): m / z[M+H] + forC 11 h 9 ClNO 2 calcd: 222.0316, found: 222.0351.

Embodiment 3

[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-position chloroindole compound and a preparation method thereof. Various N-protected indole-3-formaldehydes and N-chlorosuccinimide (NCS) were used as reaction substrates to prepare 4-position chloroindole compounds. The reaction yield can reach moderate to excellent, the reaction chemoselectivity and regioselectivity are excellent, the reaction conditions are mild, and the substrate has a wide range of application; it is easy to operate, low in cost, less in side reactions, high in product purity, and easy to separate Purification and can be applied to large-scale preparation, so the resulting product has a very good application prospect in the field of biomedicine.

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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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12C07D405/06C07D409/06
CPCC07D209/12C07D405/06C07D409/06
Inventor 刘丹丹邝广华周宜荣
Owner PINGDINGSHAN UNIVERSITY
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