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3-aroyl indole compound synthesis method

The technology of an aroyl indole compound and a synthesis method is applied in the field of synthesis of 3-aroyl indole compounds, can solve the problems of carrying out in a glove box and high reaction cost, and achieves the effects of mild reaction conditions and high yield

Inactive Publication Date: 2013-02-06
UNIV OF SCI & TECH LIAONING
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The advantage of this type of compound reaction is that the target product can be obtained in a higher yield, but the disadvantage is that most reactions can be carried out smoothly only under absolutely anhydrous conditions, which imposes strict requirements on the reaction environment and reagents.
However, the decarboxylation reaction of the above benzoylformic acid mostly needs to be carried out smoothly under the catalysis of noble metal palladium, and the reaction cost is higher

Method used

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  • 3-aroyl indole compound synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Synthesis of 5-methoxy-3-benzoyl indole

[0047] 5-Methoxyindole (0.8 mmol, 117.8 mg), benzoylformic acid (1.6 mmol, 240.2 mg), copper acetate monohydrate (0.16 mmol, 31.9 mg), silver carbonate (1.6 mmol, 441.2 mg), Dimethyl sulfoxide (4 mL) was added to a 25 mL two-necked flask equipped with a magnetic stirrer, heated to 80 °C for the reaction, followed by high performance liquid chromatography or thin layer chromatography. After the raw materials were consumed, the reaction solution was cooled. to room temperature, add ethyl acetate (5 mL) and water (5 mL), transfer it to a centrifuge tube for centrifugation, then transfer the clear liquid to a separatory funnel for separation, and dichloromethane for the aqueous phase Extraction (2×10 mL), the organic phase was washed with saturated aqueous sodium bicarbonate solution (3×10 mL), the organic layer was collected, dried over anhydrous sodium sulfate, filtered, the filtrate was collected, added with silica ge...

Embodiment 2

[0049] Example 2: Synthesis of 5-methyl-3-benzoyl indole

[0050] Combine 5-methylindole (0.8 mmol, 104.9 mg), benzoylformic acid (1.6 mmol, 240.2 mg), copper acetate monohydrate (0.16 mmol, 31.9 mg), silver carbonate (1.6 mmol, 441.2 mg), dimethine Methyl sulfoxide (4 mL) was added to a 25 mL two-necked flask equipped with a magnetic stirring bar, and the experimental procedure was as in Example 1 to obtain 144.0 mg of a pale yellow solid, which was dried in vacuo, the isolated yield was 76.5%, and the melting point was 227.0- Its structure was characterized by NMR and HRMS at 228.0°C.

[0051] 1 H NMR (500 MHz, DMSO- d 6 ): δ 11.97 (s, 1H), 8.08 (1H, s), 7.87 (s, 1H), 7.77 (d, J =8.0 Hz, 2H), 7.60 (t, J =7.0 Hz, 1H), 7.53 (t, J =7.3 Hz, 2H), 7.40 (d, J =8.5 Hz, 1H), 7.09 (d, J =7.5 Hz, 1H), 2.44 (s, 3H); 13 C NMR (125 MHz, DMSO- d 6 ) δ 190.38, 141.17, 136.16, 135.52, 131.38, 131.19, 128.81, 128.77, 127.01, 125.06, 121.69, 115.16, 112.33, 21.82. HRMS (ESI) calcd...

Embodiment 3

[0052] Example 3: Synthesis of 6-methoxy-3-benzoyl indole

[0053]6-Methoxyindole (0.8 mmol, 117.8 mg), benzoylformic acid (1.6 mmol, 240.2 mg), copper acetate monohydrate (0.16 mmol, 31.9 mg), silver carbonate (1.6 mmol, 441.2 mg), Dimethyl sulfoxide (4 mL) was added to a 25 mL two-necked flask equipped with a magnetic stirring bar, and the experimental procedure was as in Example 1 to obtain 74.4 mg of a pale yellow solid, which was dried in vacuo, the isolated yield was 37.0%, and the melting point was 226.0 -227.5℃, the structure was characterized by NMR and HRMS.

[0054] 1 H NMR (500 MHz, DMSO- d 6 ): δ 11.87 (s, 1H), 8.11 (d, J =9.0 Hz, 1H), 7.80 (s, 1H), 7.87 (s, 1H), 7.77 (d, J =7.0 Hz, 2H), 7.60 (t, J =7.0 Hz, 1H), 7.53 (t, J =7.0 Hz, 2H), 7.00 (d, J =8.0 Hz, 1H), 3.80 (s, 3H); 13 C NMR (125 MHz, DMSO- d 6 ) δ 190.28, 157.07, 141.03, 138.11, 135.26, 131.42, 128.81, 128.77, 122.59, 120.71, 115.60, 112.13, 95.77, 55.75. HRMS (ESI) calcd for C 16 H 13 NO ...

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Abstract

The invention discloses a synthesis method for 3 - aroyl indole compound with a formula I, which is characterized by comprising the following steps: taking R1-substituted indoles (II) and R2- substituted benzoylformic acid (III) as raw materials, copper salt as a catalyst, silver salt as an oxidant; and performing acylation reaction of decarboxylation in an organic solvent. According to the method, inexpensive and stable copper salt and silver salt are adopted; the reaction environment is not required to be subjected to absolute anhydrous processing; inert gas protection is not required, and the acylation reaction can be directly performed; and the reaction condition is mild and the yield is higher.

Description

technical field [0001] The invention provides a synthesis method for directly preparing 3-aroyl indole compound with copper salt as a catalyst. Background technique [0002] Indole compounds are a class of important alkaloids with significant physiological activity and widely exist in various natural products and medicines (Sundberg, R. J. The Chemistry of Indoles. Academic Press: New York, 1970; Joule, J. A. Indole and its Derivatives. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations (Eds.: Thomas, E. J.). George Thieme Verlag: Stuttgart, 2000, Category 2, Vol. 10, Chapter 10.13). In recent years, with the application of compounds containing indole structural units such as vinblastine, vincristine and vinorelbine in the treatment of cancer, the antitumor effect of these compounds has been recognized. , and a lot of research and reports have been made on it (Kidwai, M. et al. Curr. Med. Chem. 2002, 9, 1209). Especially the compounds containing 3-a...

Claims

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Application Information

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IPC IPC(8): C07D209/12
Inventor 张志强王翠苹余江龙阎京波卢公昊贾宏敏王月迟海军董岩李华吕大超张鸿
Owner UNIV OF SCI & TECH LIAONING
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