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Preparation method of diphenylphosphine substituted indole derivative

A technology of indole derivatives and indole bromide derivatives, which is applied in the preparation of diphenylphosphine-substituted indole derivatives and in the field of preparation of indole derivatives, can solve the problems of incompatibility of functional groups, harsh reaction conditions, Catalysts are expensive and other issues, to achieve the effect of facilitating industrial production, high safety, and reducing waste generation

Pending Publication Date: 2022-01-28
HENAN ACADEMY OF SCI CHEM RES INST CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods have their own advantages and disadvantages, most of which limit their application due to their relatively harsh reaction conditions, poor selectivity, expensive catalysts, and lack of compatibility with a wide range of functional groups.

Method used

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  • Preparation method of diphenylphosphine substituted indole derivative
  • Preparation method of diphenylphosphine substituted indole derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment one: the synthesis of 3-(diphenylphosphino)-1-methylindole

[0020] 0.63g (3mmol) of 3-bromo-1-methylindole, 1.17g (6mmol) of diphenylphosphine, and 1.35g (12mmol) of potassium tert-butoxide were added to 30ml of DMF, and reacted at 100°C under nitrogen protection. TLC followed the progress of the reaction until the reaction of 3-bromo-1-methylindole was complete, and the reaction ended. The reaction solution was extracted with ethyl acetate and water, the organic phase was rotary evaporated to remove the solvent, and the crude product was separated by column chromatography (the eluent was dichloromethane:petroleum ether=1:8 volume ratio) to obtain 0.78 g of the target product (produced rate of 82.5%). The analytical data of the product are as follows: 1 H NMR (400MHz, CDCl 3 ): δ7.53-7.47(m,5H),7.40-7.36(m,7H),7.33(t,J=7Hz,1H),7.11(t,J=7.5Hz,1H),7.03(d,J =3Hz,1H), 3.76(s,3H)ppm.

Embodiment 2

[0021] Embodiment two: the synthesis of 5-(diphenylphosphino)-1-methylindole

[0022] 0.63g (3mmol) of 5-bromo-1-methylindole, 1.17g (6mmol) of diphenylphosphine, and 1.35g (12mmol) of potassium tert-butoxide were added to 30ml of DMF, and reacted at 110°C under nitrogen protection. TLC followed the progress of the reaction until the 5-bromo-1-methylindole was completely reacted and the reaction was finished. The reaction solution was extracted with ethyl acetate and water, the organic phase was rotary evaporated to remove the solvent, and the crude product was separated by column chromatography (the eluent was dichloromethane:petroleum ether=1:8 volume ratio) to obtain 0.81 g of the target product (produced rate 85.7%). The analytical data of the product are as follows: 1 H NMR (400MHz, CDCl 3 ): δ7.59-7.47(m,6H),7.41-7.35(m,7H),7.30(d,J=7.5Hz,1H),7.06(d,J=7Hz,1H),3.68(s,3H )ppm.

Embodiment 3

[0023] Example 3: Synthesis of 2-(ethylformate)-3-(diphenylphosphino)-1-methylindole

[0024] 0.84g (3mmol) of 2-(ethylformyl)-3-bromo-1-methylindole, 0.84g (4.5mmol) of diphenylphosphine, and 1.01g (9mmol) of potassium tert-butoxide were added to 30ml of DMF, React at 100°C under nitrogen protection. The progress of the reaction was tracked by TLC until the reaction of 2-(methylformyl)-3-bromo-1-methylindole was complete, and the reaction ended. The reaction solution was extracted with ethyl acetate and water, the organic phase was rotary evaporated to remove the solvent, and the crude product was separated by column chromatography (the eluent was dichloromethane:petroleum ether=1:8 volume ratio) to obtain 0.89 g of the target product (produced rate of 76.7%). The analytical data of the product are as follows: 1 H NMR (400MHz, CDCl 3 ): δ7.85-7.74(m,4H),7.52-7.46(m,2H),7.44-7.38(m,5H),7.33-7.25(m,1H),7.10(d,J=8.4Hz,1H ), 6.98 (t, J = 7.2Hz, 1H), 3.92 (s, 3H), 3.74 (m, 2H...

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Abstract

The invention belongs to the technical field of preparation of organic compounds, and discloses a preparation method of a diphenylphosphine substituted indole derivative. The method comprises the steps of adding an indole bromine derivative, diphenylphosphine, potassium tert-butoxide and other alkaline compounds into a solvent, and heating and reacting under the protection of nitrogen to obtain the diphenylphosphine substituted indole derivative. Alkaline compounds such as potassium tert-butoxide are used as catalysts, noble metal catalysts are not needed, the cost is reduced, and the method is green and environment-friendly; and the method is simple to operate, high in safety, high in yield and suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and relates to a preparation method of indole derivatives, in particular to a preparation method of diphenylphosphine-substituted indole derivatives. Background technique [0002] Indole derivatives are an important class of nitrogen-containing heterocyclic compounds, which widely exist in biologically active natural alkaloids or drugs and other compounds. Drugs such as melatonin; in agriculture, it can be used to make fungicides, plant growth regulators, etc.; in terms of dyes, it can produce a variety of functional dyes. [0003] The directed substitution and functionalization of indoles are of great significance for the development of organic synthesis methodology and pharmacology. The traditional method of synthesizing indole derivatives is Fischer cyclization method (Ber.Dtsch.Chem.Ges.,1883,16:2241-2245), in addition there is cross dehydrogenation coupling reaction...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/572
CPCC07F9/5728
Inventor 陈瑨周洋申志浩代本才刘长春霍萃萌
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD