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Synthesis method of 7-azaindole substituted aryl acetate compound

A technology for aryl acetate and indole compounds, which is applied in the field of synthesis of 7-azaindole substituted aryl acetate compounds, can solve the problems of complex reaction system and poor operability, and achieve wide application The effect of prospect, high product yield and short reaction time

Pending Publication Date: 2021-03-12
JIANGSU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction system is complex, the operability is not strong, and often mixed with cycloaddition by-products

Method used

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  • Synthesis method of 7-azaindole substituted aryl acetate compound
  • Synthesis method of 7-azaindole substituted aryl acetate compound
  • Synthesis method of 7-azaindole substituted aryl acetate compound

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Experimental program
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Effect test

Embodiment 1

[0027] N-Phenyl-7-azaindole (0.2mmol), α-diazomygdalinic acid (0.24mmol), [Cp*IrCl 2 ] 2 (4mg, 2.5mol%), AgNTf 2 (8mg, 10mol%), ethanol (1mL) were added to the Schlenk reaction tube and sealed. Heated to 80°C and reacted for 20 minutes. After the reaction, the solvent was removed under reduced pressure, and the target product 3a was obtained by column chromatography with a yield of 95%. 1 H NMR (CDCl 3 ,400MHz):δ8.32(d,J=4.6Hz,1H),7.99(d,J=7.6Hz,1H),7.51-7.43(m,3H),7.38-7.33(m,2H),7.15- 7.11(m, 1H), 6.64(d, J=3.5Hz, 1H), 3.97(q, J=7.1Hz, 2H), 3.52(s, 2H), 1.10(t, J=7.1Hz, 3H). 13 C NMR (CDCl 3 ,100MHz):δ171.1,148.1,143.7,137.4,132.6,131.4,129.7,129.1,128.8,128.7,128.4,120.6,116.4,101.1,60.8,37.6,14.0.HRMS(ESI)m / z calcd for C 17 h 16 N 2 NaO 2 (M+Na) + 303.1104,found 303.1107.

Embodiment 2

[0029] N-(p-methylphenyl)-7-azaindole (0.2mmol), α-diazomygdalinic acid (0.24mmol), [Cp*IrCl 2 ] 2 (4mg, 2.5mol%), AgNTf 2 (8mg, 10mol%), ethanol (1.2mL) were added to the Schlenk reaction tube and sealed. Heated to 80°C and reacted for 30 minutes. After the reaction, the solvent was removed under reduced pressure, and the target product 3b was obtained by column chromatography with a yield of 85%. 1 H NMR (CDCl 3 ,400MHz):δ8.30(d,J=4.5Hz,1H),7.96(d,J=7.8Hz,1H),7.31-7.21(m,4H),7.11-7.08(m,1H),6.60( d, J=3.5Hz, 1H), 3.95(q, J=7.1Hz, 2H), 3.45(s, 2H), 2.42(s, 3H), 1.08(t, J=7.1Hz, 3H). 13 C NMR (CDCl 3 ,100MHz):δ171.2,148.3,143.7,138.7,134.8,132.2,131.9,129.8,129.1,129.0,128.5,120.5,116.3,100.9,60.8,37.6,21.2,14.0.HRMS(ESI)m / z calcd for 18 h 18 N 2 NaO 2 (M+Na)+317.1260, found 317.1263.

Embodiment 3

[0031] N-(p-tert-butylphenyl)-7-azaindole (0.2mmol), α-diazomygdalinic acid (0.24mmol), [Cp*IrCl 2 ] 2(4mg, 2.5mol%), AgNTf 2 (8mg, 10mol%), ethanol (1.5mL) were added to the Schlenk reaction tube and sealed. Heated to 80°C and reacted for 1 hour. After the reaction, the solvent was removed under reduced pressure, and the target product 3c was obtained by column chromatography with a yield of 89%. 1 H NMR (CDCl 3 ,400MHz):δ8.33(d,J=4.7Hz,1H),7.97(d,J=7.8Hz,1H),7.49-7.43(m,2H),7.32(d,J=3.5Hz,1H) ,7.28(d,J=8.2Hz,1H),7.12-7.08(m,1H),6.61(d,J=3.5Hz,1H),3.96(q,J=7.1Hz,2H),3.51(s, 2H), 1.39(s, 9H), 1.08(t, J=7.1Hz, 3H). 13 CNMR (CDCl 3 ,100MHz):δ171.2,151.5,148.2,143.6,134.7,131.7,129.9,129.0,128.5,128.1,125.4,120.6,116.3,100.9,61.7,37.9,34.7,31.4,14.0.HRMS(ESI)m / z forC 21 h 24 N 2 NaO 2 (M+Na) + 359.1730, found 359.1726.

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Abstract

The invention discloses a synthesis method of a 7-azaindole substituted aryl acetate compound, and relates to the fields of medicines, organic chemical engineering and fine chemical engineering. According to the method, the substituted N-aryl 7-azaindole compound, alpha-diazonium Meldrum's acid and an alcohol solvent are taken as raw materials, under the action of a reaction system taking [Cp * IrCl2]2 as a catalyst and AgNTf2 as a catalyst aid, the aryl acetate compound containing the 7-azaindole group can be synthesized at high yield through simple synthesis reaction conditions, and the method has a better application prospect.

Description

technical field [0001] The invention relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a synthesis method of a compound containing 7-azaindole substituted aryl acetate. Background technique [0002] Heterocyclic structures, especially nitrogen-containing heterocyclic structures, widely exist in natural products, alkaloids and other physiologically active molecules, so they are of great significance for the synthesis and derivatization reactions of nitrogen-containing heterocycles. The 7-azaindole (pyrrolopyridine) structure is an important class of nitrogen-containing heterocyclic structures. Molecules containing azaindole are widely used in anti-tumor, anti-cancer, anti-inflammation, anti-microbial and anti-Plasmodium falciparum. In addition, there are many applications in the field of material science, especially in OLEDs and ion sensors. Therefore, it is of great value to study the synthesis and derivatization reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 潘长多袁成
Owner JIANGSU UNIV OF TECH