KR102242238B1 - Substituted or unsubstituted 4-bromo-2-fluoroquinoline, method of the same and 2,4 substituted quinoline compounds containing them - Google Patents

Abstract

The present invention relates to a substituted or unsubstituted 4-bromo-2-fluoroquinoline compound, a method for preparing the same, and a 2,4 substituted quinoline compound including the same, tribromofluoromethane (CBr ₃ F) reacting with a substituted or unsubstituted 2-alkynyl anilines compound in an amine basic solution to prepare a substituted or unsubstituted 4-bromo-2-fluoroquinoline compound, A 2,4 substituted quinoline compound is provided by using the prepared substituted or unsubstituted 4-bromo-2-fluoroquinoline compound as a building block.

Description

Substituted or unsubstituted 4-bromo-2-fluoroquinoline compound, a method for preparing the same, and a 2,4 substituted quinoline compound comprising the same ,4 SUBSTITUTED QUINOLINE COMPOUNDS CONTAINING THEM}

The present invention relates to a substituted or unsubstituted 4-bromo-2-fluoroquinoline compound, a method for preparing the same, and a 2,4 substituted quinoline compound comprising the same, and more specifically, to tribromofluoromethane and 2,4 prepared by reacting a substituted or unsubstituted 2-alkynyl aniline compound to prepare a substituted or unsubstituted 4-bromo-2-fluoroquinoline, and using it as a building block It relates to a substituted quinoline compound.

Halogen is an element belonging to group 17 of the periodic table, and includes iodine (I), bromine (Br), chlorine (Cl), and fluorine (F). Because halogen elements are non-metallic and highly reactive, they mainly exist in the form of other elements and compounds. Specifically, since halogen has very different properties such as reactivity and selectivity for each element of halogen in the synthesis reaction of the compound, a compound having several halogens enables several reactions selectively. For this reason, halogen is most widely used as a precursor in organic reactions for synthesizing organic compounds.

Meanwhile, compounds used in natural products and pharmaceuticals are synthesized through several steps. For example. When synthesizing a drug containing quinoline, an important raw material for pharmaceuticals, as a constituent component, it is synthesized using several other reaction processes, including the process of synthesizing quinoline itself. Compounds synthesized through such a reaction process are very difficult and complex, and many studies are underway to realize simple and practical reaction conditions.

In this way, the most efficient method for manufacturing a highly functionalized complex drug is to use a building block (buidling block). The use of multiple halogens in a building block can be used as a useful building block because it can selectively enable multiple reactions. However, at present, a method for synthesizing a multiplicity building block such as synthesizing a heterocycle simultaneously with introducing several halogens has not been reported. As such, the synthesis of multiplicity building blocks still remains a difficult task, and a lot of research and development is required for practical use.

One object of the present invention is to provide a method for preparing a substituted or unsubstituted 4-bromo-2-fluoroquinoline.

Another object of the present invention is to provide a substituted or unsubstituted 4-bromo-2-fluoroquinoline compound.

Another object of the present invention is to provide a 2,4 substituted quinoline compound prepared using substituted or unsubstituted 4-bromo-2-fluoroquinoline as a multiplicity building block.

A method for preparing a substituted or unsubstituted 4-bromo-2-fluoroquinoline for an object of the present invention is to react a substituted or unsubstituted 2-alkynyl aniline compound with tribromofluoromethane. Includes.

In one embodiment, the reaction may be carried out in an amine basic solution.

In one embodiment, the reaction may be accomplished while irradiating light.

In one embodiment, the amine basic solution may be any one or more of NMM, DABCO, DBU, TEA, TMEDA, and N-benzylmethylamine.

In one embodiment, the solvent of the solution may be any one or more of DMF, DMSO, THF, 1,4-dioxane, NMP, MeCN, benzene, H2O, and DCE.

In one embodiment, the solvent of the solution may be a chlorine-based solvent.

In one embodiment, the reaction may be carried out in an oxygen-free atmosphere.

In one embodiment, the substituted or unsubstituted 2-alkynyl aniline compound may be of Formula 1 below.

<Formula 1>

In the above formula, R ¹ and R ² are each independently hydrogen, halogen, cyano, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group (Aryl), substituted or unsubstituted alkenyl Or substituted or unsubstituted alkoxy.

A substituted or unsubstituted 4-bromo-2-fluoroquinoline compound for another purpose of the present invention is the following formula (2).

<Formula 2>

In the above formula, R ¹ and R ² are each independently hydrogen, halogen, cyano, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group (Aryl), substituted or unsubstituted alkenyl Or substituted or unsubstituted alkoxy.

In one embodiment, the substituted or unsubstituted 4-bromo-2-fluoroquinoline compound may be of the formula below.

The 2,4 substituted quinoline compound for another object of the present invention uses the substituted or unsubstituted 4-bromo-2-fluoroquinoline of claim 9 as a building block.

According to the method for preparing a substituted or unsubstituted 4-bromo-2-fluoroquinoline of the present invention, tribromofluoromethane and a substituted or unsubstituted 2-alkynyl aniline compound are mixed with an amine basic solution and a solvent. And a substituted or unsubstituted 4-bromo-2-fluoroquinoline having several halogens by reacting under conditions irradiated with light. In addition, the formed substituted or unsubstituted 4-bromo-2-fluoroquinoline can be used as a building block to prepare a 2,4 substituted quinoline compound.

The terms used in the present application are only used to describe specific embodiments and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. In the present application, terms such as "comprise" or "have" are intended to designate the presence of features, steps, actions, components, parts, or combinations thereof described in the specification, but one or more other features or steps. It is to be understood that it does not preclude the possibility of addition or presence of, operations, components, parts, or combinations thereof.

Unless otherwise defined, all terms used herein including technical or scientific terms have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. Terms as defined in a commonly used dictionary should be interpreted as having a meaning consistent with the meaning in the context of the related technology, and should not be interpreted as an ideal or excessively formal meaning unless explicitly defined in the present application. Does not.

The present invention uses a tribromofluoromethane (CBr ₃ F) and a substituted or unsubstituted 2-alkynyl anilines compound, a substituted or unsubstituted 4-bromo- Prepare a 2-fluoroquinoline compound.

The tribromofluoromethane (CBr ₃ F) is a source of Br and F, and can be used to prepare a substituted or unsubstituted 4-bromo-2-fluoroquinoline compound.

The substituted or unsubstituted 2-alkynyl anilines compound is represented by the following formula (1).

<Formula 1>

In Scheme 1, R ¹ and R ² are each independently hydrogen, halogen, cyano, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group (Aryl), a substituted or unsubstituted Alkenyl or substituted or unsubstituted alkoxy.

The substituted or unsubstituted 4-bromo-2-fluoroquinoline compound of the present invention is represented by the following formula (2).

<Formula 2>

The substituted or unsubstituted 4-bromo-2-fluoroquinoline compound of the present invention is tribromofluoromethane (CBr ₃ F) and a substituted or unsubstituted 2-alkynyl aniline (2-alkynyl). anilines) is prepared through a reaction represented by Scheme 1 below using a compound.

<Reaction Scheme 1>

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In Scheme 1, R ¹ and R ² are each independently hydrogen, halogen, cyano, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group (Aryl), a substituted or unsubstituted Alkenyl or substituted or unsubstituted alkoxy.

In one embodiment, instead of the substituted or unsubstituted 2-alkynyl aniline compound, a 2-ethynyl aniline compound represented by Formula 3 may be used.

<Formula 3>

The reaction represented by Scheme 1 may be performed in an amine basic solution, and the amine basic solution is N-methylmorpholine (NMM), 1,4-diazabicyclo[2,2,2] Octane (1,4-diazabicyclo[2.2.2]octane, DABCO) 1,8-diazabicycloundec-7-ene (1,8-diazabicycloundec-7-ene, DBU), tetramethylethylenediamine (Tetramethylethylenediamine, TMEDA), triethylamine (TEA) and N-benzylmethylamine (N-benzylmethylamine) may be any one or more solutions, preferably, N-methylmorpholine (NMM) can be used as an amine basic solution. have.

The solvent of the basic amine solution is dimethylformamide (DMF), dimethyl sulfoxide (DMSO), 1,4-dioxane (1,4-dioxane), methylpyrrolidone (N-Methyl-2). -Pyrrolidone, NMP), acetonitrile (MeCN), benzene (benzene), tetrahydrofuran (THF), water (H ₂ O) and dichloroethane (dichloroethane, DCE) may be any one or more solvent . The solvent of the solution may be a chlorine-based solvent. Preferably, the solvent of the solution may be dichloroethane (DCE).

In addition, the reaction may be performed while irradiating light.

In addition, the reaction may be carried out in an oxygen-free atmosphere.

Hereinafter, a method for preparing a substituted or unsubstituted 4-bromo-2-fluoroquinoline of the present invention will be described in detail through an optimization evaluation of the following reaction conditions.

Optimization evaluation of reaction conditions

In order to evaluate the optimization of the reaction conditions, as a reactant, 0.3 mmol of tribromofluoromethane (CBr ₃ F) and 0.1 mmol of 2-ethynylaniline were used to react and substituted or provided. To obtain a ringed 4-bromo-2-fluoroquinoline (4-bromo-2-fluoroquinoline).

The reaction is represented by Scheme 2 as follows.

<Reaction Scheme 2>

To form the reaction, 0.2 mol of a solvent and a base solution (3 equivalents) were added to the mixture of reactants, and a white LED (18W, EvoluChem company) was added to 15 under an argon atmosphere. The reaction was performed for a period of time, and a substituted or unsubstituted 4-bromo-2-fluoroquinoline sample 1 to 20 was obtained due to the reaction. Details of the reaction conditions used in the preparation of Samples 1 to 20 are shown in Table 1.

The yields of Samples 1 to 20 according to the reaction were measured using gas chromatography, and the results are shown in Table 1.

Referring to Table 1, by comparing Samples 1 to 3, Sample 2 prepared except for the addition of a basic solution and Sample 3 prepared under an atmosphere not irradiated with light showed a yield of 0%, indicating a substituted or unsubstituted While it can be confirmed that the reaction for preparing the 4-bromo-2-fluoroquinoline was not made, it was confirmed that the yield was 62% in the case of Sample 1 prepared under the conditions of a basic solution and white LED (18W). It can be seen that the substituted or unsubstituted 4-bromo-2-fluoroquinoline of the present invention was synthesized.

Through Samples 4 to 8, it can be seen that the reaction performed in the presence of various amine basic solutions can produce substituted or unsubstituted 4-bromo-2-fluoroquinoline. In comparison, it can be seen that Samples 8 and 9 performed in the presence of sodium ascorbate and potassium carbonate show a yield of 0%, through which the substituted or unsubstituted 4-bromo-2 according to the present invention -It can be seen that an amine base is absolutely necessary in the reaction for preparing fluoroquinoline.

Looking at the results of Samples 11 to 18, the solvents that can be used in the reaction are dimethylformamide (DMF), dimethyl sulfoxide (DMSO), 1,4-dioxane (1,4-dioxane), Methylpyrrolidone (NMP), acetonitrile (MeCN), benzene, tetrahydrofuran (THF), water (H ₂ O) and dichloroethane (dichloroethane, DCE), it can be confirmed that it can be used in any one or more solvents, and in particular, Sample 18 prepared using dichloroethane as a solvent exhibited a yield of 85%, indicating the highest yield among the samples. This can be expected that in the reaction in which Sample 18 is prepared, chlorine in dichloroethane used as a solvent _{affects the rate of generation of CBr 2} F radicals, thereby increasing the reaction efficiency.

When comparing the results of Sample 19 with Sample 18, dichloroethane was used to predict a high yield like Sample 18, but unlike Sample 18, which showed a yield of 85%, Sample 19 was reacted in air. % Yield, showing a lower yield than Sample 19. Through this, it can be seen that the presence of oxygen significantly reduces the yield by affecting the reaction.

Checking the reaction conditions of Sample 20, Sample 20 was prepared by performing under irradiation of 365 nm mercury lamp (600W). In particular, it can be seen that the reaction time of Sample 20 was shortened from 15 hours to 2 hours by the use of a mercury lamp, indicating a very fast reaction time.

Example 1: Preparation of 4-bromo-2-fluoroquinoline compound

0.5 mmol of 2-ethynylaniline 57.5 μL, 1.5 mmol of 4-methylmorpholine (NMM) 165 μL and 1.5 M in a resealable tube equipped with a magnetic stir bar. After preparing a first mixture by mixing dichloroethane (DCE), argon gas was bubbled through the mixture for 10 minutes, and 1.5 mmol of tribromofluoromethane (CBr ₃ F) ) 23.9 μL was carefully added to prepare a second mixture. Then, the tube containing the second mixture was sealed with a silicone diaphragm screw cap, and reacted at room temperature under a white LED (18W, EvoluChem company) for 16 hours. The reaction progress was monitored by thin layer chromatography (TLC) and gas chromatography. After the reaction was completed, the second mixture was diluted with ethyl acetate (EA) and water, and the aqueous phase was further extracted with ethyl acetate. The combined organic layers were then _{dried over anhydrous MgSO 4} and concentrated in vacuo. The residue was purified by flash column chromatography with hexane/EA (8/1), and 87.8 mg of pure 0.39 mmol 4-bromo-2-fluoroquinoline in a yield of 78% Was prepared. 4-bromo-2-fluoroquinoline prepared according to Example 1 is represented by the following formula (4).

<Formula 4>

Preparation of Examples 2 to 21: Preparation of substituted or unsubstituted 4-bromo-2-fluoroquinoline compounds

Instead of 2-ethynylaniline, 2-ethynyl-4-methylaniline was used, and instead of white LED (18W, EvoluChem company), 365 nm (18W, EvoluChem compan), except for using 4-bromo-2-fluoro-6-methylquinoline (4-bromo-2-fluoro-6) according to Example 2 of the present invention through substantially the same process as in Example 1 -methylquinoline) was obtained. The 4-bromo-2-fluoro-6-methylquinoline is represented by Chemical Formula 5.

<Formula 5>

In addition, the present invention was carried out through substantially the same process as in Example 1, except that 2-ethynyl-5-methylaniline was used instead of 2-ethynylaniline. 4-bromo-2-fluoro-7-methylquinoline according to Example 3 was obtained. The 4?? bromo-2-fluoro-7-methylquinoline (4-bromo-2-fluoro-7-methylquinoline) is represented by the following formula (6).

<Formula 6>

Also, instead of 2-ethynylaniline, 4-butyl-2-ethynylaniline Except for using (4-butyl-2-ethynylaniline) and using 365 nm (18W, EvoluChem compan) instead of a white LED (18W, EvoluChem company), implementation of the present invention through substantially the same process as in Example 1 According to Example 4, 4-bromo-2-fluoro-7-methylquinoline (4-bromo-2-fluoro-6-butylquinoline) was obtained. The 4-bromo-2-fluoro-7-methylquinoline is represented by the following formula (7).

<Formula 7>

In addition, instead of 2-ethynylaniline, 2-ethynyl-4,6-dimethylaniline was used, and instead of white LED (18W, EvoluChem company), 4-bromo-2-fluoro-6,8-dimethylquinoline (4-bromo-2-fluoro-6,8-dimethylquinoline according to Example 5 of the present invention through substantially the same process as in Example 1 except that 365 nm (18W, EvoluChem compan) was used. bromo-2-fluoro-6,8-dimethylquinoline) was obtained. The 4-bromo-2-fluoro-6,8-dimethylquinoline is represented by Formula 8 below.

<Formula 8>

In addition, instead of 2-ethynylaniline, 2-ethynyl-4-methoxyaniline was used, and instead of white LED (18W, EvoluChem company), 365 nm ( 18W, EvoluChem compan) 4-bromo-2-fluoro-6-methoxyquinoline (4-bromo-2- fluoro-6-methoxyquinoline) was obtained. The 4-bromo-2-fluoro-6-methoxyquinoline is represented by Formula 9 below.

<Formula 9>

In addition, instead of 2-ethynylaniline, 2-ethynyl-5-methoxyaniline was used, and instead of white LED (18W, EvoluChem company), 365 nm ( 18W, EvoluChem compan) through substantially the same process as in Example 1, 4-bromo-2-fluoro-7-methoxyquinoline (4-bromo-2- fluoro-7-methoxyquinoline) was obtained. The 4-bromo-2-fluoro-7-methoxyquinoline is represented by Formula 10 below.

<Formula 10>

In addition, instead of 2-ethynylaniline, methyl 4-amino-3-ethynylbenzoate was used, and instead of white LED (18W, EvoluChem company), 365 4-bromo-6-carbomethoxy-2-fluoroquinoline (4-bromo) according to Example 8 of the present invention through substantially the same process as in Example 1 except that nm (18W, EvoluChem compan) was used. -6-carbomethoxy-2-fluoroquinoline) was obtained. The 4-bromo-6-carbomethoxy-2-fluoroquinoline is represented by Formula 11 below.

<Formula 11>

In addition, instead of 2-ethynylaniline, 4-amino-5-ethynylbenzonitrile was used, and instead of white LED (18W, EvoluChem company), 365 nm ( 18W, EvoluChem compan) 4-bromo-6-cyano-2-fluoroquinoline according to Example 9 of the present invention through substantially the same process as in Example 1 (4-bromo-6- cyano-2-fluoroquinoline) was obtained. The 4-bromo-6-cyano-2-fluoroquinoline is represented by the following formula (12).

<Formula 12>

In addition, instead of 2-ethynylaniline, 2-bromo-6-ethynyl-4-methylaniline (2-bromo-6-ethynyl-4-methylaniline) was used, and a white LED (18W, EvoluChem company), 4,8-dibromo-2-fluoro-6 according to Example 10 of the present invention through substantially the same process as in Example 1 except that 365 nm (18W, EvoluChem compan) was used. -Methylquinoline (4,8-dibromo-2-fluoro-6-methylquinoline) was obtained. The 4,8-dibromo-2-fluoro-6-methylquinoline (4,8-dibromo-2-fluoro-6-methylquinoline) is represented by the following formula (13).

<Formula 13>

In addition, instead of 2-ethynylaniline, 4-bromo-2-ethynylaniline was used, and instead of white LED (18W, EvoluChem company), 365 nm ( 18W, EvoluChem compan) through substantially the same process as in Example 1, 4,6-dibromo-2-fluoroquinoline according to Example 11 of the present invention (4,6-dibromo-2-fluoroquinoline ). The 4,6-dibromo-2-fluoroquinoline is represented by the following formula (14).

<Formula 14>

In addition, instead of 2-ethynylaniline, 5-bromo-2-ethynylaniline was used, and instead of white LED (18W, EvoluChem company), 365 nm ( 18W, EvoluChem compan) 4,7-dibromo-2-fluoroquinoline (4,7-dibromo-2- fluoroquinoline) was obtained. The 4,7-dibromo-2-fluoroquinoline is represented by the following formula (15).

<Formula 15>

In addition, instead of 2-ethynylaniline, 4-chloro-2-ethynylaniline was used, and instead of white LED (18W, EvoluChem company), 365 nm (18W) was used. , EvoluChem compan) 4-bromo-6-chloro-2-fluoroquinoline according to Example 13 of the present invention through substantially the same process as in Example 1 (4-bromo-6-chloro- 2-fluoroquinoline) was obtained. The 4-bromo-6-chloro-2-fluoroquinoline is represented by the following formula (16).

<Formula 16>

In addition, instead of 2-ethynylaniline, 5-chloro-2-ethynylaniline was used, and instead of white LED (18W, EvoluChem company), 365 nm (18W) was used. , EvoluChem compan) 4-bromo-7-chloro-2-fluoroquinoline according to Example 14 of the present invention through substantially the same process as in Example 1 (4-bromo-7-chloro- 2-fluoroquinoline) was obtained. The 4-bromo-7-chloro-2-fluoroquinoline is represented by the following formula (17).

<Formula 17>

In addition, instead of 2-ethynylaniline, 2,4-dichloro-6-ethynylaniline was used, and instead of white LED (18W, EvoluChem company), 4-bromo-6,8-dichloro-2-fluoroquinoline (4-bromo-6,8-dichloro-2-fluoroquinoline according to Example 15 of the present invention through substantially the same process as in Example 1 except that 365 nm (18W, EvoluChem compan) was used. bromo-6,8-dichloro-2-fluoroquinoline) was obtained. The 4-bromo-6,8-dichloro-2-fluoroquinoline is represented by the following formula (18).

<Formula 18>

In addition, instead of 2-ethynylaniline, 4-chloro-2-ethynyl-6-fluoroaniline was used, and a white LED (18W, EvoluChem company), 4-bromo-6-chloro-2,8-di according to Example 16 of the present invention through substantially the same process as in Example 1 except that 365 nm (18W, EvoluChem compan) was used. Fluoroquinoline (4-bromo-6-chloro-2,8-difluoroquinoline) was obtained. The 4-bromo-6-chloro-2,8-difluoroquinoline is represented by the following formula (19).

<Formula 19>

In addition, instead of 2-ethynylaniline, 2-ethynyl-4-fluoroaniline was used, and in place of a white LED (18W, EvoluChem company), 365 nm ( 18W, EvoluChem company) through substantially the same process as in Example 1, 4-bromo-2,6-difluoroquinoline (4-bromo-2,6- difluoroquinoline) was obtained. The 4-bromo-2,6-difluoroquinoline is represented by the following formula (20).

<Formula 20>

Instead of 2-ethynylaniline, 2-ethynyl-5-fluoroaniline was used, and instead of white LED (18W, EvoluChem company), 365 nm (18W, EvoluChem company) through substantially the same process as in Example 1, 4-bromo-2,7-difluoroquinoline according to Example 18 of the present invention (4-bromo-2,7-difluoroquinoline) Got it. The 4-bromo-2,7-difluoroquinoline is represented by Chemical Formula 21.

<Formula 21>

In addition, substantially the same process as in Example 1 except for using 2,4-diethynylnaphthalen-1-amine (2,4-diethynylnaphthalen-1-amine) instead of 2-ethynylaniline Through the 4-bromo-2-fluorobenzo[h]quinoline (4-bromo-2-fluorobenzo[h]quinoline) according to Example 19 of the present invention was obtained. The 4-bromo-2-fluorobenzo[h]quinoline is represented by the following formula (22).

<Formula 22>

In addition, the use of aniline (2-ethynylaniline) instead of 2- (oct-1-yl) aniline (2- (oct-1-yn -1-yl) aniline) and 2-ethynyl, instead, 4-bromo-3-hexyl-2-fluoroquinoline according to Example 20 of the present invention through substantially the same process as in Example 1 except that the reaction was carried out under 365 nm (600W, EvoluChem company) for 2 hours. 4-bromo-3-hexyl-2-fluoroquinoline) was obtained. The 4-bromo-3-hexyl-2-fluoroquinoline is represented by Chemical Formula 23.

<Formula 23>

In addition, instead of 2-ethynylaniline, 4,6-diethynyl-2-iodobenzene-1,3-diamine (4,6-diethynyl-2-iodobenzene-1,3-diamine) 7-amino-4-bromo-6-ethynyl-2-fluoro-8-iodoquinoline (7- amino-4-bromo-6-ethynyl-2-fluoro-8-iodoquinoline) was obtained. The 7-amino-4-bromo-6-ethynyl-2-fluoro-8-iodoquinoline is represented by the following formula It is represented by 24.

<Formula 24>

In addition, the present invention through substantially the same process as in Example 1, except for using 2-ethynyl-pyridin-3-amine (2-ethynylpyridin-3-amine) instead of 2-ethynyl aniline (2-ethynylaniline) To obtain 4-bromo-2-fluoro-1,5-naphthyrdine (4-bromo-2-fluoro-1,5-napthyrdine) according to Example 42 of. The 4-bromo-2-fluoro-1,5-napthyrdine is represented by the following formula (25).

<Formula 25>

Although the above has been described with reference to preferred embodiments of the present invention, those skilled in the art will be able to variously modify and change the present invention without departing from the spirit and scope of the present invention described in the following claims. You will understand that you can.

Claims (11)

Comprising reacting tribromofluoromethane with a substituted or unsubstituted 2-alkynyl aniline compound of Formula 1 below,
A method for preparing a substituted or unsubstituted 4-bromo-2-fluoroquinoline of Formula 2 below.
<Formula 1>

(In Formula 1, R1 and R2 are each independently hydrogen, halogen, cyano, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or 1 to 10 alkoxy.)
<Formula 2>

(In Chemical Formula 2, R1 and R2 are each independently hydrogen, halogen, cyano, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or 1 to 10 alkoxy.)
The method of claim 1,
The reaction is characterized in that it takes place in an amine basic solution,
A method for producing a substituted or unsubstituted 4-bromo-2-fluoroquinoline.
The method of claim 1,
The reaction is characterized in that it takes place while irradiating light,
A method for producing a substituted or unsubstituted 4-bromo-2-fluoroquinoline.
The method of claim 2,
The amine basic solution is characterized in that it is any one or more of NMM, DABCO, DBU, TEA, TMEDA, and N-benzylmethylamine,
A method for producing a substituted or unsubstituted 4-bromo-2-fluoroquinoline.
The method of claim 2,
The solvent of the solution is any one or more of DMF, DMSO, THF, 1,4-dioxane, NMP, MeCN, benzene, H2O, and DCE,
A method for producing a substituted or unsubstituted 4-bromo-2-fluoroquinoline.
The method of claim 2,
The solvent of the solution is characterized in that the chlorine-based solvent,
A method for producing a substituted or unsubstituted 4-bromo-2-fluoroquinoline.
The method of claim 1,
The reaction is characterized in that to be carried out in an oxygen-free atmosphere,
A method for producing a substituted or unsubstituted 4-bromo-2-fluoroquinoline.
delete Substituted or unsubstituted 4-bromo-2-fluoroquinoline compound of Formula 2 below:
<Formula 2>

In Formula 2, R1 and R2 are each independently hydrogen, halogen, cyano, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or 1 To 10 alkoxy.
The method of claim 9,
The substituted or unsubstituted 4-bromo-2-fluoroquinoline compound is a substituted or unsubstituted 4-bromo-2-fluoroquinoline compound, characterized in that it has the following formula:

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