Unlock instant, AI-driven research and patent intelligence for your innovation.
Ortho-halogenated phenylpyridine ketone compound and preparation method thereof
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
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
View PDF3 Cites 0 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
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) copperhalide, 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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
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 layerchromatography 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.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
PUM
Login to View More
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 hydrocarbonhalogenation 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) copperhalide, 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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More 
Login to View More