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A kind of synthetic method of 3,3'-diindoleethane compounds

A technology of indoleethane and compounds, which is applied in the field of synthesis of 3,3'-diindoleethane compounds, can solve the problems of high production cost and narrow adaptability of reaction substrates, etc., and achieve the effect of high yield

Active Publication Date: 2021-04-23
NANCHANG HANGKONG UNIVERSITY
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  • Abstract
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Problems solved by technology

However, so far, there are many methods for synthesizing 3,3'-diindolylmethane and its derivatives in the prior art (see 3) Chin.J.Org.Chem.2012,32,1195~1207), and 3 , the methods for 3'-diindolyleethane and its derivatives are still very limited (see 1) Bioorganic & Medicinal Chemistry Letters 24(2014) 5059–5062; 2) Synlett 2013,24,1931–1936; 4) J.Chem. Research (S), 1997, 424–425; 5) J.Am.Chem.Soc., Vol.120, No.13, 1998), and these methods need expensive catalytic systems such as noble metal palladium, alkali and high temperature It can only be carried out under low conditions, and has the defects of high production cost and narrow adaptability of reaction substrates

Method used

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  • A kind of synthetic method of 3,3'-diindoleethane compounds
  • A kind of synthetic method of 3,3'-diindoleethane compounds
  • A kind of synthetic method of 3,3'-diindoleethane compounds

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Experimental program
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Effect test

Embodiment 11

[0052]

[0053] Add p-methoxystyrene (0.2mmol) shown in formula I-1, N-ethylindole (1mmol, 5 equivalents) shown in formula II-2, Cu(OTf) in Schlenk tube lock reactor 2 (0.02mmol, 10mol%), Ir(ppy) 3 (0.02mmol, 10mol%), K 2 S 2 o 8 (0.4mmol, 2 equivalents), and MeCN (2mL), then under the protection of argon, the reaction was stirred at room temperature for 12 hours, after the completion of the reaction monitored by TLC or GC-MS, the solvent was distilled off under reduced pressure, and the residue was subjected to Column chromatography separation (eluent: n-hexane / ethyl acetate) gave the target product of formula III-2. Yield 55%. 1 H NMR (400MHz, CDCl 3 )δ:7.65-7.55(m,1H),7.46-7.37(m,1H),7.35-7.22(m,2H),7.17-7.07(m,5H),6.98(s,2H),6.81-6.68( m,2H),6.46-6.45(m,1H),4.60-4.49(m,1H),4.18-4.07(m,2H),4.01-3.94(m,2H),3.73(s,3H),3.67- 3.64(m,1H),3.37-3.32(m,1H),1.41(t,J=7.2Hz,3H),1.30-1.22(m,3H). 13 C NMR (101MHz, CDCl 3)δ: 157.7, 137.7, 136.2, 135.6, 129.0, 128.3, 127.6, 12...

Embodiment 12

[0055]

[0056] Add p-methoxystyrene (0.2mmol) shown in formula I-1, 5-cyano-N-methylindole (1mmol, 5 equivalents) shown in formula II-3 in the Schlenk lock reactor , Cu(OTf) 2 (0.02mmol, 10mol%), Ir(ppy) 3 (0.02mmol, 10mol%), K 2 S 2 o 8 (0.4mmol, 2 equivalents), and MeCN (2mL), then under the protection of argon, the reaction was stirred at room temperature for 12 hours, after the completion of the reaction monitored by TLC or GC-MS, the solvent was distilled off under reduced pressure, and the residue was subjected to Column chromatography separation (eluent: n-hexane / ethyl acetate) gave the target product of formula III-3. Yield 52%. 1 H NMR (400MHz, CDCl 3 )δ:7.56(s,1H),7.52(s,1H),7.37-7.26(m,4H),7.12(d,J=7.2Hz,2H),7.05(s,1H),6.80(d,J =7.6Hz,2H),6.69(s,1H),4.41(t,J=7.2Hz,1H),3.79(s,6H),3.70(s,3H),3.56-3.50(m,1H),3.39 -3.34(m,1H).; 3 C NMR (101MHz, CDCl 3 )δ: 158.3, 138.6, 138.1, 136.2, 129.2, 128.7, 128.1, 127.9, 127.2, 125.3, 124.5, 124.3, 120.9, 120.2, 114....

Embodiment 13

[0058]

[0059] Add p-methoxystyrene (0.2mmol) shown in formula I-1, 7-methoxycarbonyl-N-methylindole (1mmol, 5 equivalents) shown in formula II-4 in the Schlenk lock reactor ), Cu(OTf) 2 (0.02mmol, 10mol%), Ir(ppy) 3 (0.02mmol, 10mol%), K 2 S 2 o 8 (0.4mmol, 2 equivalents), and MeCN (2mL), then under the protection of argon, the reaction was stirred at room temperature for 12 hours, after the completion of the reaction monitored by TLC or GC-MS, the solvent was distilled off under reduced pressure, and the residue was subjected to Column chromatography separation (eluent: n-hexane / ethyl acetate) gave the target product of formula III-4. Yield 64%. 1 H NMR (400MHz, CDCl 3 )δ: 7.68(m, 3H), 7.51(d, J=7.6Hz, 2H), 7.12-7.04(m, 3H), 6.98-6.92(m, 2H), 6.75(d, J=8Hz, 2H) ,6.47(s,1H),4.51(t,J=7.2Hz,1H),3.93(s,6H),3.81(s,3H),3.73(s,3H),3.68(s,3H),3.60- 3.55(m,1H),3.35-3.29(m,1H) 13 C NMR (101MHz, CDCl 3 )δ: 168.1, 168.1, 157.8, 137.0, 134.3, 133.8, 132.4, 130.8, 130.8, 130...

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Abstract

The invention discloses a new method for preparing 3,3'-diindoleethane derivatives. The method takes vinyl compounds as starting materials and directly reacts with indole compounds to obtain 3,3'-diindole The ethane derivative has the advantages of simple process, mild reaction conditions and wide adaptability of reaction substrates.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing 3,3'-diindoleethane compounds. Background technique [0002] Indole and its derivatives are raw materials for the production of a series of pharmaceuticals, biologically active substances, dyes, spices and chemical products, and have a wide range of uses, and diindolylmethane and diindolyethane are one of the important derivatives , they not only have significant biological activity, but also are key intermediates for the synthesis of many kinds of alkaloids with complex structures. [0003] 3,3'-Diindolyleethane and its derivatives have been proven to have good biological activities, such as MRSA PK inhibition of enzyme activity (see 1) Bioorganic & Medicinal Chemistry Letters 24 (2014) 5059–5062); and as a drug synthesis intermediate For example, synthesis of (+)-tjipanazole (see 2) Synlett 2013, 24, 1931–1936) and the like. However, so far...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12C07D209/08C07D209/10C07D405/14C07D519/00
CPCC07D209/08C07D209/10C07D209/12C07D405/14C07D519/00
Inventor 宋仁杰李金恒秦景灏
Owner NANCHANG HANGKONG UNIVERSITY
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