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Phosphine ligand for indole skeleton as well as preparation method and application of phosphine ligand

A phosphine ligand, indole phosphine technology, applied in the field of organic compounds and synthesis, can solve problems such as poor catalytic activity

Inactive Publication Date: 2017-12-08
THE HONG KONG POLYTECHNIC UNIV SHENZHEN RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to provide a phosphine ligand of a 3-(disubstituted phosphino)-1-alkyl-2-substituted phenyl-indole skeleton, aiming to solve the problem of using the existing phosphorus ligand as a cross-coupling reaction The problem of poor catalytic activity in the case of synergists of transition metal catalysts

Method used

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  • Phosphine ligand for indole skeleton as well as preparation method and application of phosphine ligand
  • Phosphine ligand for indole skeleton as well as preparation method and application of phosphine ligand
  • Phosphine ligand for indole skeleton as well as preparation method and application of phosphine ligand

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preparation example Construction

[0056] As a specific embodiment, a method for preparing a phosphine ligand of a 3-(disubstituted phosphino)-1-alkyl-2-substituted phenyl-indole skeleton is provided, comprising the following steps:

[0057] S01. After mixing substituted acetophenone and N-alkylphenylhydrazine, adding phosphoric acid as a catalyst, after stirring, adding polyphosphoric acid, and performing a heating reaction to prepare 2-(substituted phenyl)-1-alkane Base-1H-indole intermediate, or the substituted acetophenone and N-alkylphenylhydrazine are mixed, then add acetic acid and ethanol to react at 70-80°C for 0.5-1.5 hours, and then remove all solvents under reduced pressure , then add polyphosphoric acid, carry out heating reaction, prepare 2-(substituted phenyl)-1-alkyl-1H-indole intermediate, wherein, the heating temperature of described heating reaction is 80-120 ℃, and reaction time is 1 -2 hours;

[0058] S02. Dissolve the 2-(substituted phenyl)-1-alkyl-1H-indole intermediate and N-bromosuccin...

Embodiment 1

[0180] Example 1: Synthesis of 3-(dicyclohexylphosphino)-1-methyl-2-phenyl-1H-indole

[0181] In a 250 ml round bottom flask, add 10.4 g of N-methyl-2-phenylindole (50 mmol), then add 80 ml of anhydrous dimethylformamide and stir evenly. Then, a mixed solution of 10.6 g of N-bromosuccinimide (60 mmol) and 60 ml of anhydrous dimethylformamide was added and reacted at room temperature for 2 hours. When the reaction was completed, the reaction mixture was poured into ice water, and then 100 ml of dichloromethane and 50 ml of water were added. Then add 150 milliliters of water to wash each organic phase in five times again, and combine the organic phases. After all the solution was sucked off under reduced pressure, the concentrated reaction mixture was purified by column chromatography to obtain 12.3 grams of white powdery pure product 3-bromo-1-methyl-2-phenyl-1H-indole intermediate, the yield 86%. 1H NMR (400MHz, CDCl 3 ) 3.76 (s, 3H), 7.50-7.56 (m, 3H), 7.65-7.72 (m, 5H), ...

Embodiment 2

[0183] Example 2: Synthesis of 3-(dicyclohexylphosphino)-2-(2-methoxyphenyl)-1-methyl-1H-indole

[0184] In a 100 ml round bottom flask, add 6.9 ml of 2'-methoxyacetophenone (50 mmol) and 7.1 ml of N-methylphenylhydrazine (60 mmol), then slowly add 10 ml of phosphoric acid, and stir evenly at room temperature for 0.5 Hour. Then slowly add 50 grams of polyphosphoric acid. With the progress of the reaction, the system exothermic obviously. Then the mixture was slowly heated to 120°C and kept at 120°C for 1 hour. The mixture was poured into ice water to terminate the reaction, then 200 ml of ether was added to the system, and 200 ml of ether was added three times for extraction. The organic phases were combined and dried over anhydrous sodium sulfate. After all the solution was sucked off under reduced pressure, the concentrated reaction mixture was purified by column chromatography, and then the product was obtained as light yellow powder. Then add 15 milliliters of normal h...

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Abstract

The invention provides a phosphine ligand for a 3-(disubstituted phosphino)-1-alkyl-2-substituted phenyl-indole skeleton as well as a preparation method and application of the phosphine ligand. The structure of the phosphine ligand for the 3-(disubstituted phosphino)-1-alkyl-2-substituted phenyl-indole skeleton is shown as the following formula I: (shown in the description), wherein Z is carbon or nitrogen, R is alkyl, substituted alkyl, olefin, aryl or fluorine, R1 is alkyl, substituted alkyl or aryl, R2 is alkyl, substituted alkyl or fluorine, and R3 is alkyl, substituted alkyl or aryl.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and synthesis, and relates to a phosphine ligand with an indole skeleton and its preparation method and application, in particular to a 3-(disubstituted phosphino)-1-alkyl-2-substituted phenyl - Phosphine ligands with indole skeletons and their preparation methods and applications. Background technique [0002] Transition metal-catalyzed cross-coupling reactions are one of the important methods for forming carbon-carbon and carbon-heteroatom bonds. In the field of carbon-carbon bond formation, Suzuki, Hiyama, Negishi, Kumada, Stille and α-monoarylation of carbonyl compounds (α- Cross-coupling reactions such as arylation of carbonyl compounds) are common methods for preparing biaryl and / or related compounds. In this field, the selective cross-coupling reaction of reactants by transition metal catalysts remains a great challenge, especially in the Suzuki coupling reaction of aryl chlorid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6506C07F9/6558C07F15/00B01J31/24C07C1/32C07C15/14C07C41/30C07C43/205C07C67/343C07C69/76C07C45/68C07C49/784C07C201/12C07C205/36C07C253/30C07C255/54C07C47/575C07D213/16C07D307/46C07D333/22C07D409/04C07D405/04
CPCB01J31/2447B01J2231/4205B01J2231/4227B01J2231/4277C07C1/32C07C41/30C07C45/68C07C67/343C07C201/12C07C253/30C07C2531/24C07D213/16C07D307/46C07D333/22C07D405/04C07D409/04C07F9/6506C07F9/65583C07F15/0066C07C15/14C07C43/205C07C69/76C07C49/784C07C205/36C07C255/54C07C47/575
Inventor 邝福儿苏秋铭周永健原安莹蔡珮盈
Owner THE HONG KONG POLYTECHNIC UNIV SHENZHEN RES INST
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