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Method for continuously preparing dicarbonyl indole compound by utilizing micro-channel reaction device

A microchannel reaction, biscarbonyl indole technology, applied in chemical instruments and methods, chemical/physical processes, chemical/physical/physical chemical processes, etc. Potential for industrial scale-up, easy operation and control of the preparation process, and mild reaction conditions

Active Publication Date: 2017-07-07
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved in the present invention is to develop a novel method for preparing biscarbonylindole compounds, which overcomes the problems of long reaction process cycle and expensive catalysts in traditional oxidation systems

Method used

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  • Method for continuously preparing dicarbonyl indole compound by utilizing micro-channel reaction device
  • Method for continuously preparing dicarbonyl indole compound by utilizing micro-channel reaction device
  • Method for continuously preparing dicarbonyl indole compound by utilizing micro-channel reaction device

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Experimental program
Comparison scheme
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Embodiment 1

[0034] The synthesis of embodiment 1 compound 3a:

[0035] Dissolve 10mmol (1.20g) phenylacetaldehyde in 10mL dimethyl sulfoxide (dimethyl sulfoxide) to obtain a homogeneous solution A, add it to syringe pump a; dissolve 5mmol (1.27g) iodine in 10mL dimethicone In methyl sulfoxide (dimethyl sulfoxide), a homogeneous solution B was obtained, which was added to syringe pump b; 10 mmol (1.31 g) of N-methylindole was dissolved in 20 mL of dimethyl sulfoxide (dimethyl In sulfoxide), obtain homogeneous solution C, add in the syringe pump c; The injection flow rate of syringe pump a, b is 0.4ml / min, and the injection flow rate of syringe pump c is 0.6ml / min; The first microchannel reaction Reactor reaction volume V=5ml, reaction time 6.25min, the second microchannel reactor reaction volume V=5ml, reaction time 3.57min; The first, second microchannel reactor internal diameter=0.5mm; The first microchannel reactor temperature The temperature of the second microchannel reactor was 110°...

Embodiment 2

[0036] The synthesis of embodiment 2 compound 3b:

[0037] The method is the same as in Example 1, except that the compound I is p-fluorophenylacetaldehyde, the reaction parameters are shown in Table 2, the yield is 85%, and the product 3b is obtained after separation by column chromatography; 1 H NMR (400MHz, CDCl 3 )δ8.51–8.40(m,1H),8.18–8.11(m,2H),7.83(d,J=5.1Hz,1H),7.39(dd,J=5.4,2.6Hz,3H),7.16(t ,J=8.7Hz,2H),3.84(d,J=10.1Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ192.11, 187.16, 167.90, 165.34, 139.78, 137.88, 133.34, 133.25, 130.12, 130.09, 126.55, 124.44, 123.73, 122.80, 116.25, 116.05, 112.92, 122.80, 116.25, 116.05, 112.92, 110.9 ] + Calcd for C 17 h 12 FNO 2 304.0744found 304.0747.

Embodiment 3

[0038] The synthesis of embodiment 3 compound 3c:

[0039] The method is the same as in Example 1, except that the compound I is p-chlorophenylacetaldehyde, the reaction parameters are shown in Table 2, the yield is 82%, and the product 3c is obtained after separation by column chromatography; 1 H NMR (400MHz, CDCl 3 )δ8.52–8.39(m,1H),8.05(d,J=8.6Hz,2H),7.82(s,1H),7.46(d,J=8.6Hz,2H),7.39(dd,J=6.2 ,3.4Hz,3H),3.83(s,3H); 13 C NMR (100MHz, CDCl 3 )δ192.36,186.81,140.95,139.78,137.84,131.99,131.82,129.20,126.50,124.43,123.72,122.77,112.84,110.16,33.92; HRMS(TOF)m / z[M+Na] + Calcd for C 17 h 12 ClNO 2 320.0449found 320.0443.

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Abstract

The invention relates to a method for continuously preparing a dicarbonyl indole compound by utilizing a micro-channel reaction device. A phenylacetaldehyde compound I and an indole compound II are used as reaction raw materials, and in an iodine / dimethyl sulfoxide oxidation system, a continuous two-step reaction is performed in the micro-channel reaction device to obtain the dicarbonyl indole compound III; the reaction process is as shown in a reaction formula: (with reference to the specification). The method disclosed by the invention is simple, convenient, safe and efficient to operate and mild in reaction condition, has excellent substrate universality and also can be implemented after reaction amplification.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for continuously preparing biscarbonylindole compounds by utilizing a microchannel reaction device. Background technique [0002] Indole and its derivatives widely exist in nature and have strong physiological and pharmaceutical activities. The C-H functionalization reaction of indole plays an important role in the synthesis of natural products and drugs. Dicarbonyl compounds have two adjacent Carbonyl, which has special chemical properties, is widely used as a precursor or intermediate for drug synthesis to synthesize biscarbonylindole compounds through cheap iodine oxidative coupling. [0003] At present, the preparation methods of biscarbonylindole compounds mainly include: (1) acetophenone, indole, and iodine synthesize biscarbonylindole compounds under the catalysis of tetrahydropyrrole. The disadvantages of this method are mainly long reaction cycle and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12C07D409/06C07D405/06C07D401/06B01J19/00
CPCB01J19/0006B01J19/0093C07D209/12C07D401/06C07D405/06C07D409/06
Inventor 郭凯花加伟方正郭诗宇欧阳平凯
Owner NANJING TECH UNIV
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