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Ortho-halogenated phenylpyridine ketone compound and preparation method thereof

A compound, haloalkyl technology, applied in the field of ortho-halogenated phenylpyridine ketones and their preparation, can solve the problems of large environmental pollution, strong toxicity, poor selectivity, etc.

Active Publication Date: 2019-12-13
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the halogenated reagents commonly used in the synthesis of aromatic halogenated compounds mainly include the following categories: (1) simple halogen, which is gas or highly volatile, has strong toxicity, poor reaction selectivity, and large environmental pollution; (2) N-halogenated Succinimide, the atom economy of this type of halogenated reagent is poor; (3) copper halide, the halogenated reagent uses metal halides, which is highly toxic and costly; (4) halide / oxidant (oxidative halogenation), The reaction system is complex and requires the use of oxidizing reagents; but the above halogenated reagents still have their own shortcomings

Method used

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  • Ortho-halogenated phenylpyridine ketone compound and preparation method thereof
  • Ortho-halogenated phenylpyridine ketone compound and preparation method thereof
  • Ortho-halogenated phenylpyridine ketone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of 2-Bromophenylpyridyl Methanone

[0023]

[0024] Phenylpyridinyl ketone (36.6 mg, 0.2 mmol), dibromohydantoin (85.8 mg, 0.3 mmol) and Pd(OAc) 2 (4.5mg, 0.02mmol), added 2mL of chlorobenzene, reacted at 120°C for 12h, purified by thin layer chromatography to obtain 26.5mg of 2-bromophenylpyridyl ketone, yield 50.6%, 1 H NMR (400MHz, CDCl 3 ): δ=8.73(d, J=4.8Hz, 1H), 8.20(d, J=8.0Hz, 1H), 7.98-7.94(dt, J1=7.6Hz, J2=2.0Hz, 1H), 7.68(dd , J1=7.6Hz, J2=1.2Hz, 1H), 7.55-7.50(m, 2H), 7.47(dd, J1=7.6Hz, J2=1.2Hz, 1H), 7.43-7.39(m, 1H)ppm; 13 C NMR (100MHz, CDCl 3 ): δ=195.9, 153.5, 149.4, 140.3, 137.1, 133.1, 131.6, 129.9, 127.1, 127.0, 124.0, 120.1ppm.

Embodiment 2

[0026] Synthesis of 2-Bromophenylpyridyl Methanone

[0027]

[0028] Phenylpyridyl ketone (36.5 mg, 0.2 mmol), dibromohydantoin (85.8 mg, 0.3 mmol) and Pd(TFA) 2 (0.02mmol), add 2mL of chlorobenzene, react at 120°C for 12h, no product is formed.

Embodiment 3

[0030] Synthesis of 2-Bromophenylpyridyl Methanone

[0031]

[0032] Phenylpyridyl ketone (36.6 mg, 0.2 mmol), dibromohydantoin (85.8 mg, 0.3 mmol) and Fe(OAc) 2 (0.02mmol), add 2mL of chlorobenzene, react at 120°C for 12h, no product is formed.

[0033] The catalyst Fe(OAc) 2 Replaced by Cu(OAc) 2 Or under the condition of not adding any catalyst, there is also no product generation.

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Abstract

The invention relates to an ortho-halogenated phenylpyridine ketone compound and a preparation method thereof. According to the invention, dibromohydantoin or dichlorohydantoin is taken as a halogenating reagent, and the ortho-halogenation of a diarylketone compound is realized through a palladium-catalyzed selective hydrocarbon halogenation reaction, so an ortho-halogenated diarylketone compoundis obtained. Compared with other halogenating reagents, the dibromohydantoin and the dichlorohydantoin used in the invention have the advantages of low cost, high active halogen content, good storagestability, economic performance and the like. A selective synthesis method of the halogenated diarylketone compound provided by the invention is low in cost, relatively small in environmental damage and suitable for industrial production, and provides a new method for synthesis of a hepatitis B treatment drug, namely lonafarnib.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an ortho-halogenated phenylpyridine ketone compound and a preparation method thereof. Background technique [0002] Aromatic halogenated compounds are an important class of organic synthesis intermediates, which are widely used in the synthesis of dyes, pesticides, spices and drugs. At present, the halogenated reagents commonly used in the synthesis of aromatic halogenated compounds mainly include the following categories: (1) simple halogen, which is gas or highly volatile, has strong toxicity, poor reaction selectivity, and large environmental pollution; (2) N-halogenated Succinimide, this type of halogenated reagent has poor atom economy; (3) copper halide, the halogenated reagent uses metal halides, which is highly toxic and costly; (4) halide / oxidant (oxidative halogenation), The reaction system is complex and requires the use of oxidizing reagents; ho...

Claims

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Application Information

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IPC IPC(8): C07D213/50
CPCC07D213/50
Inventor 刘祈星陈永盛张银陈淡宜文思妙妙赵蓉蓉刘毅恒周海峰
Owner CHINA THREE GORGES UNIV
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