Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis method of 5-iodoindole compound

A technology of an iodoindole compound and a synthetic method is applied in the field of organic synthesis and achieves the effects of high reaction efficiency, high yield and simple operation

Inactive Publication Date: 2021-03-12
NORTHWEST UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although natural products linked to the C5 position of indole exist widely, so far, there are very few reports on the direct functionalization of indole at the C5 position of indole, and there is still a lack of a general and effective strategy to deal with the function of the C5 position of the indole ring. change

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of 5-iodoindole compound
  • Synthesis method of 5-iodoindole compound
  • Synthesis method of 5-iodoindole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] In a 10 mL one-neck flask, add 0.5 mmol indole-3-carbaldehyde 1a, 0.5 mmol N-iodosuccinimide 2a (NIS), add solvent dichloromethane (3 mL), and add 1 mmol dropwise with stirring BF 3 . Et 2 O, reacted at room temperature for 4 h. After the reaction, extraction was performed, and the solvent was removed by rotary evaporation of the reaction solution under reduced pressure, and the residue was purified by flash silica gel column to obtain the corresponding 5-iodoindole compound 3a in a yield of 78%.

[0019]

[0020] Compound 3a is a white solid, melting point: 185-186 o C; Eluant: ethyl acetate / petroleumether (1:2, R f = 0.30). 1 H NMR (400 MHz, DMSO) δ 12.27 (s, 1H), 9.92 (s, 1H), 8.44 (s, 1H), 8.29 (d, J = 3.1 Hz, 1H), 7.53 (dd, J = 8.5, 1.4 Hz, 1H), 7.37(d, J = 8.5 Hz, 1H); 13 C NMR (101 MHz, DMSO) δ 185.2, 138.9, 136.2, 131.6, 129.2, 126.7, 117.2, 115.0, 86.6; , 1088, 878, 789, 666, 608 cm -1 ; HRMS (ESI) m / z calculated for C 9 H 6 INNaO[M+Na] + :...

Embodiment 2

[0022] Into a 10 mL one-neck flask, add 0.5 mmol indole-3-ethanone 1b, 0.5 mmol iodine, add solvent chloroform (3 mL), and dropwise add 1 mmol BF under stirring 3 . Et 2 O, reacted at room temperature for 4 h. After the reaction was completed, extraction was performed, and the solvent was removed by rotary evaporation of the reaction solution under reduced pressure, and the residue was purified by flash silica gel column to obtain the corresponding 5-iodoindole compound 3b in a yield of 43%.

[0023]

[0024] Compound 3b is a white solid, melting point: 133-134 o C; Eluant: ethyl acetate / petroleumether (1:2, R f = 0.30). 1 H NMR (400 MHz, DMSO) δ 12.08 (s, 1H), 8.52 (d, J =1.6 Hz, 1H), 8.31 (s, 1H), 7.48 (dd, J = 8.5, 1.7 Hz, 1H), 7.33 (d, J = 8.5Hz, 1H), 2.44 (s, 3H); 13 C NMR (101 MHz, DMSO) δ 192.8, 135.8, 135.1, 130.8, 129.7, 127.8, 116.0, 114.6, 86.2, 27.2; , 880, 786, 737, 529 cm -1 ; HRMS (ESI) m / z calculated for C 10 H 8 INNaO[M+Na] + : 307.9543; fo...

Embodiment 3

[0026] In a 10 mL one-neck flask, add 0.5 mmol of indole-3-methyl ester 1c, 0.5 mmol of N-iodosuccinimide 2a, add solvent trichloromethane (3 mL), and dropwise add 1 mmol of trifluorotrifluorocarbon under stirring Acetic acid (TFA) for 4 h at room temperature. After the reaction was completed, extraction was performed, and the solvent was removed by rotary evaporation of the reaction solution under reduced pressure, and the residue was purified by flash silica gel column to obtain the corresponding 5-iodoindole compound 3c in a yield of 61%.

[0027]

[0028] Compound 3c is a yellow solid, melting point: 184-185 o C; Eluant: ethyl acetate / petroleumether (1:2, R f = 0.30). 1 H NMR (400 MHz, DMSO) δ 8.33 (s, 1H), 8.09 (s, 1H), 7.47 (d, J= 8.2 Hz, 1H), 7.35 (d, J = 8.4 Hz, 1H), 3.81 (s, 3H); 13 C NMR (101MHz, DMSO) δ 164.5, 135.6, 133.4, 130.5, 128.8, 128.2, 115.0, 105.7, 85.9, 50.9; IR: 3273, 2923, 1680, 1446, 1357, 119, 4, 79,777 536 cm -1 ;HRMS (ESI) m / z calculated...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthesis method of a 5-iodo indole compound, and the method comprises the following steps: by using an indole compound as a starting raw material and Niodo succinimide or iodine as an iodine source, carrying out free radical reaction in a halogenated organic solvent at normal temperature and normal pressure in the presence of Lewis acid to synthesize the 5-iodo indole compound. The synthesis method is mild in condition, wide in substrate application range, good in functional group tolerance and free of metal participation, and has the advantages of being easy to operate, environmentally friendly, high in specific regioselectivity and the like.

Description

technical field [0001] The invention relates to a method for synthesizing a 5-iodoindole compound, and belongs to the technical field of organic synthesis. Background technique [0002] The indole skeleton is a very important structural unit in constituting natural products, pharmaceuticals, agrochemicals and functional materials. For nearly a hundred years, synthetic chemists have been working to functionalize indoles. One side of the indole ring structure is a pyrrole ring, and the other side is a benzene ring. The high activity position is on the pyrrole side (C2 and C3 positions), so the functionalization on the C2 and C3 positions of the indole ring is relatively easy. The functionalization of the C2 and C3 positions of the inole ring has been extensively developed, and there are many reports in the literature. However, the position-selective functionalization of the phenyl ring side (C4, C5, C6, C7 positions) of indole remains a great challenge. In the currently dev...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D209/12C07D209/42
CPCC07D209/12C07D209/42
Inventor 王永强王昭阳
Owner NORTHWEST UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com