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4-iodophenyl substituted carborane derivative and preparation method thereof

A carborane and derivative technology, applied in the field of 4-iodophenyl substituted carborane derivatives and their preparation, can solve the problems of low yield, harsh reaction conditions and the like, and achieve high synthesis yield and preparation amount The effect of increasing, increasing solubility

Pending Publication Date: 2020-12-15
YANCHENG INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to overcome the problem that the iodine-substituted phenylcarborane precursor needs to carry out the butyllithium debromination process in the prior art, which has harsh reaction conditions and low yield, the present invention proposes a 4-iodophenyl-substituted carborane Alkane derivatives and methods for their preparation

Method used

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  • 4-iodophenyl substituted carborane derivative and preparation method thereof
  • 4-iodophenyl substituted carborane derivative and preparation method thereof
  • 4-iodophenyl substituted carborane derivative and preparation method thereof

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preparation example Construction

[0050] The embodiment of the present invention also provides a preparation method of the 4-iodophenyl substituted carborane derivative, comprising the following steps:

[0051] (1) Using the Sonogashira coupling reaction, and Under the palladium / copper catalyst effect, generate triazene-containing alkyne intermediates, wherein X is hydrogen, halo, triazene, alkyl, alkoxy, nitrogen heterocyclyl or ethynyl, when X When it is a hydrogen group, a halo group, an alkyl group, an alkoxy group or an azacyclic ring group, the alkyne intermediate containing a triazene is

[0052]

[0053] When X is an ethynyl group, the triazene-containing alkyne intermediate is

[0054]

[0055] in, The synthesis process refers to Journal of Organic Chemistry, 2014, 79(4), 1594-1610;

[0056] The consumption of described palladium / copper catalyst satisfies catalytic effect and gets final product, preferred following consumption: Relative to The molar consumption of, the consumption of de...

Embodiment 1

[0080] Example 1 The preparation of 1-(4-iodophenyl)-2-phenyl-1,2-carborane (R 1 =H, refer to DaltonTransactions, 2019, 48(33), 12549-12559)

[0081] (1) Synthesis of 3,3-diethyl-1-(4-iodophenyl)-1-triazene with reference to Journal of Organic Chemistry, 2014,79(4), 1594-1610: 25.0g (114.2mmol ) 4-iodoaniline was added to a mixed solvent consisting of 35mL of acetonitrile, 230mL of water and 35mL of concentrated hydrochloric acid (37% by mass fraction) (cooled to 0°C) to obtain a light gray suspension; 8.66g (125.6mmol) Sodium nitrite was dissolved in 23mL of water, cooled with ice and added to the above suspension to obtain a green solution, and stirred for 30min; 23.7g (171.2mmol) of potassium carbonate and 17.9mL of diethylamine (171.2mmol) were added to 175mL of water, cooled with ice, and then slowly added to the above green solution, and continued stirring for 1h. After the reaction was completed, it was extracted twice with ethyl acetate, the organic phase was separat...

Embodiment 2

[0085] Example 2 Preparation of 1-(4-iodophenyl)-2-(4-bromo)phenyl-1,2-carborane (Cab1, R 2 =Br)

[0086] (1) The preparation of 3,3-diethyl-1-(4-iodophenyl)-1-triazene is the same as in Example 1;

[0087] (2) In a 100 ml reaction tube, mix 6.0g (19.8mmol) 3,3-diethyl-1-(4-iodophenyl)-1-triazene and 3.9g (21.8mmol) 4- Bromophenylacetylene was added to a mixed solvent of 30 mL tetrahydrofuran and 15 mL triethylamine to obtain a reaction mixture; the reaction mixture was degassed twice through liquid nitrogen cooling-vacuumizing-thawing, and at the same time observe whether there was any After obvious bubbles escaped and no bubbles emerged, nitrogen was charged, and 417mg (0.6mmol) of Pd(PPh) was added under the protection of nitrogen. 3 ) 2 Cl 2 and 226mg (1.2mmol) of CuI, the reaction mixture was warmed up to 80°C, and the reaction was continued for 10h. After the reaction was completed, the solvent was removed by rotary evaporation, and the initial product was subjected ...

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Abstract

The invention discloses a 4-iodophenyl carborane derivative and a preparation method thereof. Commercialized organic reagents 4-iodoaniline and a diacetonitrile decaborate complex and several easily-synthesized substituted alkynes are adopted as the starting raw materials, carrying out diazotization reaction, Sonogashira coupling reaction, iodine exchange and alkyne addition reaction are carried out to form a series of 4-iodophenyl carborane with different substituent groups. The preparation method provided by the invention has the advantages of strong group applicability, easy purification and separation, high synthesis yield and high reference value.

Description

technical field [0001] The invention belongs to the technical field of carborane, and in particular relates to a 4-iodophenyl substituted carborane derivative and a preparation method thereof. Background technique [0002] Carborane is an atomic cluster compound formed by boron and carbon, which is an extremely stable icosahedral closed carborane, in which the electrically neutral C 2 B 10 h 12 That is, o-carborane is particularly important, and it is widely used in many fields such as heat-resistant polymers, medicine, and optoelectronic materials. For example, due to the high boron content in carborane molecules, it can be introduced into boron neutron flotation therapy to treat diseases such as cancer. In addition, because this compound conforms to Huckel's rule, it is highly aromatic and quite stable to heat. Like aromatic hydrocarbons, carborane can also undergo electrophilic aromatic substitution reactions. In recent years, the introduction of carborane into organi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/027
Inventor 王兆进关荣锋杨秀丽邵荣
Owner YANCHENG INST OF TECH
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