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Preparation method of 7-amide indole compound

A compound and indole technology, which is applied in the field of ruthenium-catalyzed preparation of 7-amide indole compounds, and achieves the effects of simple preparation method, low reaction cost and simple operation

Active Publication Date: 2020-11-06
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Direct regioselective functionalization of indole benzene ring moieties remains a challenge for synthetic chemists

Method used

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  • Preparation method of 7-amide indole compound
  • Preparation method of 7-amide indole compound
  • Preparation method of 7-amide indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] At room temperature, N-pivaloyl indole (0.2mmol), 3-phenyloxazolone (0.6mmol), [Ru(p-cymene)Cl 2 ] 2 (5mol%), AgSbF 6 (20mol%), pivalic acid (3 equiv.) and HFIP (2.0 mL). Stir at room temperature. TLC tracking detection reaction. After 24 hours, the reaction was stopped. Water and dichloromethane were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three to five times with dichloromethane. All organic layers were combined, dried with anhydrous sodium sulfate, concentrated, separated by column chromatography (5% ethyl acetate petroleum ether solution), obtained 43.6 mg of product, and the yield was 68%. The reaction process is shown in the following formula:

[0030]

[0031] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0032] 1 H NMR (600MHz, CDCl 3 )δ10.30(brs,1H),8.22(dd,J=5.9,3.2Hz,1H),8.11–8.09(m,2H),7.67(d,J=3.9Hz,1H),7.56–7.50(m ,3H),7.40–7.38(m,2H),6.68...

Embodiment 2

[0034]At room temperature, N-pivaloyl indole (0.2mmol), 3-phenyloxazolone (0.6mmol), [Cp*IrCl 2 ] 2 (5mol%), AgSbF 6 (20mol%), pivalic acid (3 equiv.) and HFIP (2.0 mL). Stir at room temperature. TLC tracking detection reaction. After 24 hours, the reaction was stopped. Water and dichloromethane were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three to five times with dichloromethane. All organic layers were combined, dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography (5% ethyl acetate petroleum ether solution) to obtain 13.5 mg of product with a yield of 21%. The reaction process is shown in the following formula:

[0035]

[0036] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0037] 1 H NMR (600MHz, CDCl 3 )δ10.30(brs,1H),8.22(dd,J=5.9,3.2Hz,1H),8.11–8.09(m,2H),7.67(d,J=3.9Hz,1H),7.56–7.50(m ,3H),7.40–7.38(m,2H),6.68(d,J=3....

Embodiment 3

[0039] At room temperature, N-pivaloyl indole (0.2mmol), 3-phenyloxazolone (0.6mmol), [Ru(p-cymene)Cl 2 ] 2 (5mol%), AgSbF 6 (20mol%), benzoic acid (3 equiv.) and HFIP (2.0 mL). Stir at room temperature. TLC tracking detection reaction. After 24 hours, the reaction was stopped. Water and dichloromethane were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three to five times with dichloromethane. All organic layers were combined, dried with anhydrous sodium sulfate, concentrated, separated by column chromatography (5% ethyl acetate petroleum ether solution), obtained 22.4 mg of product, and the yield was 35%, and the reaction process was shown in the following formula:

[0040]

[0041] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0042] 1 H NMR (600MHz, CDCl 3 )δ10.30(brs,1H),8.22(dd,J=5.9,3.2Hz,1H),8.11–8.09(m,2H),7.67(d,J=3.9Hz,1H),7.56–7.50(m ,3H),7.40–7.38(m,2H)...

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Abstract

The invention discloses a preparation method of a 7-amide indole compound. The method comprises the following steps of: in an HFIP solvent, synthesizing the 7-amide indole compound at room temperatureby using [Ru (p-cymene) Cl2] 2 and AgSbF6 as catalysts, using pivalic acid as an additive and using an indole compound and an oxazolone compound as substrates. The reaction raw materials are cheap and easy to obtain; the preparation method is simple; ruthenium is used as the catalyst, so that the reaction cost is low, the yield is high, the operation is simple; and the method is suitable for synthesizing different types of 7-amide indole compounds. The method disclosed by the invention can be used for synthesizing a series of 7-amide indole compounds, and the synthesized product can be used as an intermediate compound for further constructing a complex active compound; and meanwhile, the compound has great drug activity potential.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a ruthenium-catalyzed method for preparing 7-amide indole compounds. Background technique [0002] The indole skeleton is widely distributed in natural products and pharmaceutically active molecules as the dominant skeleton, and it is considered to be the most attractive class of nitrogen-containing heterocycles. Transition metal-catalyzed functionalization of carbon-hydrogen bonds can directly and efficiently construct new carbon-carbon bonds and carbon-heteroatom bonds. In recent decades, a large number of transition metal-catalyzed methods have been developed for the synthesis of substituted indoles. Due to the higher reactivity of the pyrrole ring moiety compared to the benzene ring moiety, most of the reported methods were used for the synthesis of 2-substituted and 3-substituted indoles. Direct regioselective functionalization of indole benzene ring moieties r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/26C07D209/14C07D209/08C07D209/12
CPCC07D209/26C07D209/14C07D209/08C07D209/12
Inventor 宋增强周健民盛耀光梁广
Owner WENZHOU MEDICAL UNIV
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