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Method for green oxidation synthesis of N-substituted 2H-indazole compound

A technology for oxidative synthesis and compound, applied in the direction of organic chemistry, can solve problems such as limited application prospects, and achieve the effects of high product yield, wide substrate applicability, and easy operation.

Active Publication Date: 2021-03-30
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, electrochemically induced direct C–H amination reactions have rarely been reported, except for the recent work by Li pinhua’s group.
However, the cathode material used in this method is expensive platinum, which greatly limits the application prospect of this method.

Method used

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  • Method for green oxidation synthesis of N-substituted 2H-indazole compound
  • Method for green oxidation synthesis of N-substituted 2H-indazole compound
  • Method for green oxidation synthesis of N-substituted 2H-indazole compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] 2-Phenyl-2H-indazole (0.3mmol, 58.2mg), pyrazole (1.5eq., 30.6mg), potassium persulfate (3.0eq., 243mg), and water 3mL were sequentially added into a 25mL Schleck tube. Reaction at 80°C for 12h. After the reaction was completed (monitored by TLC), the heating was stopped, and after cooling to room temperature, ethyl acetate (EA) was added for extraction (3×10 mL), the organic layers were combined and dried, concentrated under reduced pressure, column chromatography, and petroleum ether: ethyl acetate The 80:1 ester mixture was used as the eluent, and the eluent containing the target product was collected and distilled under reduced pressure to obtain 70.2 mg of the target product as a white solid, with a yield of 90%.

[0022] M.p.132-133℃. 1 H NMR (400MHz, CDCl 3 )δ7.85(d, J=1.8Hz, 1H), 7.81(d, J=8.8Hz, 1H), 7.60(d, J=8.6Hz, 1H), 7.55(d, J=2.4Hz, 1H) ,7.44–7.38(m,6H),7.21(dd,J=8.2,6.8Hz, 1H),6.50(t,J=2.0Hz,1H). 13 C NMR (100MHz, CDCl 3 )δ148.02,142.46,...

Embodiment 2

[0024]

[0025] In a 25mL Schleck tube, add 2-(3-methoxyphenyl)-2H-indazole (0.3mmol, 67.2mg), pyrazole (1.5 eq., 30.6mg), potassium persulfate (4.0eq., 324mg ), water 3mL. Reaction at 60°C for 12h. After the reaction was completed (monitored by TLC), the heating was stopped, and after cooling to room temperature, ethyl acetate (EA) was added for extraction (3×10 mL), the organic layers were combined and dried, concentrated under reduced pressure, column chromatography, and petroleum ether: ethyl acetate The 80:1 ester mixture was used as the eluent. The eluent containing the target product was collected and distilled under reduced pressure to obtain 72.2 mg of the target product as a white solid with a yield of 83%.

[0026] M.p.93-94℃. 1 H NMR (400MHz, CDCl 3 )δ7.87(d, J=1.8Hz, 1H), 7.81(d, J=8.8Hz, 1H), 7.59(d, J=8.6Hz, 1H), 7.56(d, J=2.4Hz, 1H) ,7.41(dd,J=8.2,7.2Hz,1H),7.31(d,J=7.8Hz, 1H),7.21(dd,J=8.4,6.8Hz,1H),6.98–6.93(m,3H), 6.51(t,J=2.0Hz,1H),3.77(s,3H). 13 C...

Embodiment 3

[0028]

[0029] Add 2-(4-methoxyphenyl)-2H-indazole (0.3mmol, 67.2mg), pyrazole (1.5eq., 30.6mg), potassium persulfate (2.0eq., 163mg), water 3mL. Reaction at 80°C for 12h. After the reaction was completed (monitored by TLC), the heating was stopped, and after cooling to room temperature, ethyl acetate (EA) was added for extraction (3×10 mL), the organic layers were combined and dried, concentrated under reduced pressure, column chromatography, and petroleum ether: ethyl acetate The 80:1 ester mixture was used as the eluent, and the eluent containing the target product was collected and distilled under reduced pressure to obtain 56.5 mg of the target product as a white solid, with a yield of 65%.

[0030] M.p.100-101℃. 1 H NMR (400MHz, CDCl 3 )δ7.84(d, J=1.6Hz, 1H), 7.79(d, J=8.8Hz, 1H), 7.59(d, J=8.6Hz, 1H), 7.53(d, J=2.4Hz, 1H) ,7.41–7.36(m,1H),7.35–7.31(m,2H),7.19 (dd,J=8.2,7.0Hz,1H),6.48(t,J=2.0Hz,1H),3.84(s,3H ). 13 C NMR (100MHz, CDCl 3)δ 159.79, 147.82, 142.30...

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Abstract

The invention relates to a green oxidation synthesis method of an N-substituted 2H-indazole compound shown as a formula (I); the method comprises the following steps: dissolving a 2H-indazole compoundshown as a formula (II) and pyrazole in a solvent, adding an oxidant, reacting at 60-100 DEG C for 10-12 hours, and carrying out aftertreatment on the obtained reaction solution to obtain the N-substituted 2H-indazole compound shown as the formula (I). The molar ratio of the 2H-indazole compound shown in the formula (II) to the pyrazole to the oxidizing agent is 1: 1.5-3: 2-4; and the oxidant issodium persulfate, potassium persulfate or ammonium persulfate; according to the method, the N-substituted indazole compound is synthesized by adopting the cheap and easily available oxidant potassiumperoxodisulfate, so that the method is simple and convenient to operate, high in product yield and wide in substrate applicability, and meets the requirements of green chemistry.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a new method for green oxidation synthesis of N-substituted 2H-indazole compounds. Background technique [0002] Indazole compounds, as a special skeleton of nitrogen-containing heterocyclic compounds, are widely used in the fields of medicinal chemistry and material science. Especially indazole has anti-inflammatory, anti-tumor, anti-bacterial, HIV protease inhibitory, anti-cancer, anti-platelet, anti-depressant and other drugs. Some commercially available drugs, such as Bendazak (non-steroidal anti-inflammatory drug), pazopanib or votriene (tyrosine kinase inhibitor), MK-4827 (anticancer drug), etc. azole skeleton. Importantly, indazole derivatives have excellent photophysical properties and can be used as fluorescent probes. On the other hand, amines and azoles are widely found in natural products and pharmaceuticals. [0003] In recent years, visible light-med...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/56
CPCC07D231/56
Inventor 谢媛媛王凯魏婷婷侯加浩
Owner ZHEJIANG UNIV OF TECH
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