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Synthetic method for N-acylindole chiral boron compound

A technology for acylindole and boron compounds, applied in the field of synthesis of N-acylindole chiral boron compounds, achieving the effects of wide application range, mild reaction conditions, and easy availability of raw materials

Inactive Publication Date: 2018-06-12
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, α,β-unsaturated N-acylindoles have not been applied to asymmetric borylation reactions, and their products contain indole groups with potential biological activity.

Method used

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  • Synthetic method for N-acylindole chiral boron compound
  • Synthetic method for N-acylindole chiral boron compound
  • Synthetic method for N-acylindole chiral boron compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Under nitrogen protection, copper iodide CuI (1.9mg, 0.01mmol), (R,S)-Josiphos (9.6mg, 0.015mmol), potassium phosphate K 3 PO 4 (4.2mg, 0.02mmol), pivalyl alcohol t-AmOH (1.0mL), after stirring at room temperature for 30 minutes, add bis-pinacolyl diborane 3 (55.9mg, 0.22mmol) and pivalyl alcohol t-AmOH (0.5 mL), stirred at room temperature for 10 minutes. Then (E)-N-(3-phenylacryloyl)indole 2a (50mg, 0.2mmol) and pivalyl alcohol t-AmOH (0.5mL) were added and stirred at 25°C for 20 hours. After cooling to room temperature, filter through diatomaceous earth, wash the filter cake with ethyl acetate (20 mL), and concentrate the filtrate under reduced pressure. After separation by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=60:1), the white solid product 1a (71mg, yield 96%, ee value 95% ). The target product was confirmed by NMR and high-resolution mass spectrometry, and the ee value was determined by chiral high-p...

Embodiment 2

[0027] The reaction steps and operation are the same as in Example 1, except that the copper salt is cuprous bromide. The reaction was stopped, and the target product 1a (64 mg, yield 85%, ee value 95%) was obtained after post-processing. It shows that cuprous bromide can also be used as a catalyst for the reaction, but it is not the best catalyst.

Embodiment 3

[0029] The reaction steps and operation are the same as in Example 1, and the difference from Example 1 is that the alkali is sodium carbonate. The reaction was stopped, and the target product 1a (56 mg, yield 75%, ee value 90%) was obtained after post-processing. It shows that sodium carbonate can also be used as the base of the reaction, but it is not the best base.

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Abstract

The invention discloses a synthetic method for an N-acylindole chiral boron compound with potential biological activity. The chiral boron compound is synthesized through an asymmetric boronizing reaction with alpha, beta-unsaturated N-acylindole and bis(pinacolato)diboron as raw materials and chiral ligand copper salt as a catalyst. Compared with a reported method for synthesis of a chiral boron compound, the synthetic method provided by the invention has the advantages of easily-available raw materials, simple and convenient operation, wide application range, mild reaction conditions, containment of an indole substituent in a product, and potential biological activity.

Description

technical field [0001] The invention discloses a synthesis method of N-acylindole chiral boron compound with potential biological activity. Using α,β-unsaturated N-acylindole and bis-pinacolyl diborane as raw materials and chiral ligand copper salt as catalyst, chiral boron compounds were synthesized by asymmetric boronation. Compared with the reported methods for synthesizing chiral boron compounds, the present invention has easy-to-obtain raw materials, simple operation, wide application range and mild reaction conditions. The product contains indole substituents and has potential biological activity. Background technique [0002] Chiral boron compounds are important organic reagents and have a wide range of applications in the fields of industry, agriculture, and medicine. The indole group is an extremely important functional group, which can greatly change the biological activity and physical properties of the compound, and is widely used in pharmaceutical molecules and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07B2200/07C07F5/027
Inventor 郭腾龙姜权彬余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI