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Method for preparing bi-indolyl fluorene derivative

A technology for bis-indolyl fluorene and derivatives is applied in the field of preparing bis-indolyl fluorene derivatives, and achieves the effects of mild reaction conditions, few operation steps and high synthesis efficiency

Active Publication Date: 2014-06-11
山东禾雅生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the use of bisaryl ketones, or condensation reactions between fused ring ketones and indole

Method used

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  • Method for preparing bi-indolyl fluorene derivative
  • Method for preparing bi-indolyl fluorene derivative
  • Method for preparing bi-indolyl fluorene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: This example is the synthesis of 9,9'-bis(7-methyl-3-indolyl)fluorene; using 9-fluorenone and 7-methylindole as raw materials, the reaction formula is as follows:

[0036]

[0037] Implementation steps:

[0038] 0.180 g (1 mmol) of 9-fluorenone, 0.328 g (2.5 mmol) of 7-methylindole and 0.096 g (0.1 mmol) of methanesulfonic acid were placed in a reaction flask, 25 mL of methanol was added, and heated to reflux (reaction solution The temperature is about 65° C.), followed by TLC until the end of the reaction, cooled to room temperature, and suction filtered to obtain a solid. The solid was recrystallized from DMSO to give pure product (74% yield).

[0039] Product data: 1 H NMR (400 MHz, DMSO-d 6 ) δ 10.81 (s, 1H), 7.94 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 7.6 Hz, 1H), 7.36 (t, J = 7.4 Hz, 1H), 7.19 (t, J = 7.4 Hz, 1H), 6.77 (d, J = 6.5 Hz, 2H), 6.70 – 6.58 (m, 2H), 2.40 (s, 3H); 13 C NMR (101 MHz, DMSO-d 6 ) δ 152.91, 139.48, 136.96, 127.67 (d, ...

Embodiment 2

[0040] Example 2: This example is the synthesis of 9,9'-bis(5-bromo-3-indolyl)fluorene; using 9-fluorenone and 5-bromoindole as raw materials, the reaction formula is as follows:

[0041]

[0042] Implementation steps:

[0043] 0.180 grams (1 mmol) of 9-fluorenone, 0.485 grams (2.5 mmol) of 5-bromoindole and 0.096 grams (0.1 mmol) of methanesulfonic acid were placed in a reaction flask, 25 mL of ethanol was added, and heated to reflux (reaction temperature About 78°C), followed by TLC until the end of the reaction, cooled to room temperature, and suction filtered to obtain a solid. The solid was recrystallized from dimethylsulfoxide to obtain pure product (yield 88%).

[0044] Product data: 1 H NMR (400 MHz, DMSO-d 6 ) δ 11.17 (s, 1H), 8.00 (d, J = 7.5 Hz, 1H), 7.49 – 7.37 (m, 2H), 7.35 – 7.24 (m, 2H), 7.10 (dd, J = 8.6, 1.5 Hz, 1H), 6.98 (d, J = 2.2 Hz, 1H), 6.74 (s, 1H); 13 C NMR (101 MHz, DMSO-d 6 ) δ 152.02, 139.41, 136.14, 128.08, 127.84, 125.86, 125.57, 123...

Embodiment 3

[0045]Example 3: This example is the synthesis of 9,9'-bis(2-methyl-3-indolyl)fluorene; using 9-fluorenone and 2-methylindole as raw materials, the reaction formula is as follows:

[0046]

[0047] Implementation steps:

[0048] 0.180 grams (1 mmol) of 9-fluorenone, 0.328 grams (2.5 mmol) of 2-methylindole and 0.096 grams (0.1 mmol) of methanesulfonic acid were placed in a reaction flask, 25 mL of propanol was added, heated to reflux (reaction Liquid temperature is about 97°C), TLC tracking until the end of the reaction, cooled to room temperature, and suction filtration to obtain a solid. The solid was recrystallized from dimethyl sulfoxide to obtain pure product (97% yield).

[0049] Product data: 1 H NMR (400 MHz, DMSO-d 6 ) δ 10.71 (s, 1H), 7.91 (d, J = 7.5 Hz, 1H), 7.53 (d, J = 7.6 Hz, 1H), 7.35 (t, J = 7.4 Hz, 1H), 7.16 (t, J = 7.2 Hz, 2H), 6.84 (t, J = 7.5 Hz, 1H), 6.54 (t, J = 7.1 Hz, 2H), 1.73 (s, 3H); 13 C NMR (101 MHz, DMSO-d 6 ) δ 153.50, 139.32...

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Abstract

The invention relates to a method for preparing a bi-indolyl fluorene derivative. According to the method, fluorenone and indole are taken as reactants and are dissolved in a solvent so as to react at 25DEG C-100DEG C to obtain the bi-indolyl fluorene derivative, wherein acid is taken as a catalyst, the molar ratio of fluorenone, indole and catalyst is 1:(1-4):(0.05-0.2). According to the method, the raw materials and the catalyst are cheap and are easy to obtain, and the reaction conditions are mild; the bi-indolyl fluorene derivative is built with one step through cascade reaction, the method has few operation steps, is convenient to separate and purify, and has high synthesis efficiency; and the method also can be used for preparing other large conjugated system molecules with applied research significance through reaction of aromatic heterocycle, benzene ring and fluorenone.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing bisindolylfluorene derivatives. Background technique [0002] Bisindole compounds are metabolites of many terrestrial and marine organisms. They have a wide range of pharmaceutical activities, can promote the metabolism of estrogen in the human body, and have good inhibitory activity on the growth of cancer cells. For example, bisindole methane can induce cancer in the human body. Apoptosis without affecting normal cell growth. In particular, it has a good inhibitory effect on the growth of breast cancer cells; it has antibacterial activity and can relieve fibromyalgia pain. In biology, bisindole can also be used as a fluorescent probe, etc. [0003] For the synthesis of bisindole, bisindolylmethane is the most widely and deeply studied. It is commonly used to catalyze the synthesis of aldehydes and indole in the presence of substances such ...

Claims

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Application Information

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IPC IPC(8): C07D209/08C07D471/04
CPCC07D209/08C07D471/04
Inventor 安礼涛安晓伟孙小军朱凤霞周建峰吕蒙陈雄
Owner 山东禾雅生物科技有限公司
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