JP5478095B2 - Method for producing arylpyridines - Google Patents

Description

  The present invention relates to a method for producing aryl pyridines useful as a raw material for producing pharmaceuticals and agricultural chemicals.

  As a method for producing arylpyridines by activating the carbon-hydrogen bond of pyridine and coupling with aryl halides, by reacting pyridine and benzene iodide under microwave irradiation using an iridium complex as a catalyst. It is disclosed that a mixture of three isomers, namely 2-phenylpyridine, 3-phenylpyridine and 4-phenylpyridine can be obtained (for example, see Non-Patent Document 1). In addition, pyridine is oxidized to pyridine-N-oxide, and then a palladium complex or a palladium complex and a copper compound are used as a catalyst to activate a carbon-hydrogen bond at the ortho position of the pyridine-N-oxide to produce aryl halides. A method of producing 2- (aryl) pyridine by obtaining 2- (aryl) pyridine-N-oxide by coupling with hydrogen and further hydrogen reduction in the presence of a palladium catalyst is disclosed (for example, non- (See Patent Documents 2 and 3). However, in the method described in Non-Patent Document 1, the substrate is limited to iodobenzene, and the total yield of the three isomers remains at a maximum of 41%. Furthermore, since the reaction requires microwave irradiation, it is not necessarily advantageous as an industrial production method. In addition, the methods of Non-Patent Documents 2 and 3 are not necessarily advantageous as an industrial production method because the obtained arylpyridines are limited to 2- (aryl) pyridine and require three-step reaction for production. Absent.

  There has been no report on a method for producing arylpyridines in which the carbon-hydrogen bond of pyridine is activated using the nickel catalyst of the present invention and coupled with aryl halides.

Organic Letters, 10, 4673, 2008. Journal of American Chemical Society, 127, 18020, 2005. Angelwandte Chemie, International Edition, 45, 7781, 2006.

  An object of the present invention is to provide a method for producing arylpyridines simply and in high yield, using aryl halides and pyridine as raw materials.

As a result of intensive studies to solve the above problems, the present inventors have found that in the presence of potassium tert-butoxide, a reducing agent, and a nickel catalyst, a compound represented by the general formula Ar-X (1)
(In the formula, Ar represents an optionally substituted phenyl group or naphthyl group, and X represents iodine, bromine or chlorine.)
It has been found that a mixture of arylpyridines can be efficiently produced by reacting an aryl halide represented by general formula (II) with pyridine, and the present invention has been completed.

That is, the present invention provides a compound of the general formula Ar-X (1) in the presence of potassium tert-butoxide, a reducing agent and a nickel catalyst.
(In the formula, Ar represents an optionally substituted phenyl group or naphthyl group, and X represents iodine, bromine or chlorine.)
The present invention relates to a method for producing a mixture of arylpyridines, which comprises reacting an aryl halide represented by general formula (II) with pyridine.

  The phenyl group or naphthyl group represented by Ar may be substituted with a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenyl group, or the like.

  Specific examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Specific examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, and cyclobutyl group. And a cyclopropylmethyl group. Specific examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropyloxy group, a cyclopropyloxy group, a butoxy group, an isobutyloxy group, a sec-butyloxy group, and a tert-butyloxy group. , Cyclobutyloxy group, cyclopropylmethyloxy group and the like.

  Next, the production method of the present invention will be described in detail.

  Examples of the nickel catalyst that can be used in the present invention include nickel fluoride, nickel chloride, nickel bromide, nickel iodide, nickel acetate, nickel nitrate, nickel oxide, nickel sulfate, nickel hydroxide, nickel carbonate, and stearic acid. Nickel, di (acetylacetonato) nickel, bis (hexafluoroacetylacetonato) nickel, dibromo (dimethoxyethane) nickel, allyl (cyclopentadienyl) nickel, bis (1,5-cyclooctadiene) nickel, bis ( Cyclopentadienyl) nickel, bis (methylcyclopentadienyl) nickel, bis (ethylcyclopentadienyl) nickel, bis (tetramethylcyclopentadienyl) nickel, (cyclopentadienyl) (carbonyl) nickel dimer, etc. Raised Rukoto can. Bis (cyclopentadienyl) nickel is preferred because of its good yield.

  The molar ratio of the nickel compound to the aryl halides (1) is preferably 1: 1 to 1: 100, and more preferably 1: 5 to 1:50 in terms of a good yield.

  The solvent that can be used in the present invention may be any solvent that does not inhibit the reaction. Specifically, tetrahydrofuran, diethyl ether, 1,4-dioxane, 1,2-dimethoxyethane, benzene, toluene, anisole and the like can be used. These may be mentioned, and these may be used in combination as appropriate. Further, pyridine may be used as a substrate and solvent. Pyridine is preferred because of its good yield.

  The molar ratio of pyridine and aryl halides is not particularly limited as long as pyridine is in an excess amount.

  Specific examples of the reducing agent that can be used in the present invention include phosphines such as triphenylphosphine, boron such as triethylborane, tributylborane, borane-THF complex, and 9-borabicyclo [3.3.1] nonane. Examples include compounds, organic aluminums such as trimethylaluminum and triethylaluminum, organic zincs such as diethylzinc, and organic substances such as azobisisobutyronitrile. Triphenylphosphine is preferable in terms of good yield. The molar ratio between the nickel compound and the reducing agent is preferably 1: 0.5 to 1:10, and more preferably 1: 1 to 1: 5 in terms of good yield.

  The molar ratio of the nickel compound and potassium tert-butoxide is preferably 1: 1 to 1: 100, and more preferably 1:10 to 1:50 in terms of good yield.

  When the reaction is carried out in a closed system, it can be carried out at a pressure appropriately selected from the range of atmospheric pressure (0.1 MPa) to 1.0 MPa, but the reaction proceeds sufficiently even under atmospheric pressure. Further, the atmosphere during the reaction is preferably performed under an inert gas such as argon or nitrogen.

  The method for isolating the product arylpyridines after the reaction is not particularly limited, but includes solvent extraction, column chromatography, preparative thin layer chromatography, preparative liquid chromatography, recrystallization, distillation, sublimation, etc. The object can be obtained by a general-purpose method.

  By using the production method of the present invention, arylpyridines useful as a raw material for production of medical and agricultural chemicals can be obtained simply and in high yield.

  Hereinafter, although an example is given and the present invention is explained still in detail, the present invention is not limited to these.

  Example 1

スクリューキャップ付試験管（１０ｍＬ）に、ビス（シクロペンタジエニル）ニッケル ０．００４７ｇ（０．０２５ｍｍｏｌ）、トリフェニルホスフィン ０．００６６ｇ（０．０２５ｍｍｏｌ）およびカリウムｔｅｒｔ−ブトキシド ０．０５６ｇ（０．５ｍｍｏｌ）を加え、容器内をアルゴンで置換した。この混合物にアルゴン雰囲気下で、ブロモベンゼン ０．０５３ｍＬ（０．５ｍｍｏｌ）とピリジン ２．５ｍＬを加え、１０分間攪拌した。この混合溶液を１００℃で１２時間攪拌した。反応溶液を室温まで冷却し、水 ２ｍＬとトルエン ３ｍＬを加えて分液した。有機層を濃縮した残渣をシリカゲルカラムクロマトグラフィー（溶離液 ヘキサン：クロロホルム＝１００：０〜２：１）に通すことにより、２−フェニルピリジン（０．０２５０ｇ、収率３２％）、３−フェニルピリジン（０．０２３４ｇ、収率３０％）、４−フェニルピリジン（０．００６０ｇ、収率８％）をそれぞれ無色液体、黄色液体、白色固体として得た。

In a test tube (10 mL) with a screw cap, 0.0047 g (0.025 mmol) of bis (cyclopentadienyl) nickel, 0.0066 g (0.025 mmol) of triphenylphosphine and 0.056 g (0.5 mmol) of potassium tert-butoxide ) Was added, and the inside of the container was replaced with argon. Under an argon atmosphere, 0.053 mL (0.5 mmol) of bromobenzene and 2.5 mL of pyridine were added to the mixture and stirred for 10 minutes. The mixed solution was stirred at 100 ° C. for 12 hours. The reaction solution was cooled to room temperature, and 2 mL of water and 3 mL of toluene were added for liquid separation. The residue obtained by concentrating the organic layer was passed through silica gel column chromatography (eluent hexane: chloroform = 100: 0 to 2: 1) to give 2-phenylpyridine (0.0250 g, yield 32%), 3-phenylpyridine. (0.0234 g, yield 30%) and 4-phenylpyridine (0.0060 g, yield 8%) were obtained as a colorless liquid, a yellow liquid, and a white solid, respectively.

2-Phenylpyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.68 (td, J = 4.8, 1.3 Hz, 1H), 7.98 (dd, J = 7.9 Hz, 1.5 Hz, 2H) , 7.73-7.68 (m, 2H), 7.49-7.43 (m, 2H), 7.42-7.37 (m, 1H), 7.22-7.16 (m, 1H).
¹³ C-NMR (CDCl ₃ , ppm): δ 157.4, 149.6, 139.3, 136.6, 128.9, 128.6, 122.0, 120.5.
MS: 155 (M ^<+> ).
3-phenylpyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.84 (dd, J = 2.3, 0.6 Hz, 1H), 8.58 (dd, J = 4.8, 1.6 Hz, 1H) 7.85 (ddd, J = 7.9, 2.3, 1.7 Hz, 1H), 7.57 (dd, J = 8.3, 1.2 Hz, 2H), 7.49-7.44. (M, 2H), 7.42-7.37 (m, 1H), 7.34 (ddd, J = 7.9, 4.8, 0.8 Hz, 1H).
¹³ C-NMR (CDCl ₃ , ppm): δ 148.3, 148.2, 137.7, 136.5, 134.3, 129.0, 128.0, 127.0, 123.4.
MS: 155 (M ^<+> ).
4-phenylpyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.66 (dd, J = 4.5, 1.6 Hz, 2H), 7.74 (d, J = 7.0 Hz, 2H), 7.53 -7.42 (m, 5H).
¹³ C-NMR (CDCl ₃ , ppm): δ 150.2, 148.3, 138.1, 129.1, 129.0, 127.0, 121.6.
MS: 155 (M ^<+> ).
Example 2

スクリューキャップ付試験管（１０ｍＬ）に、ビス（シクロペンタジエニル）ニッケル ０．００４７ｇ（０．０２５ｍｍｏｌ）、トリフェニルホスフィン ０．００６６ｇ（０．０２５ｍｍｏｌ）およびカリウムｔｅｒｔ−ブトキシド ０．０５６ｇ（０．５ｍｍｏｌ）を加え、容器内をアルゴンで置換した。この混合物にアルゴン雰囲気下で、４−ブロモアニソール ０．０６３ｍＬ（０．５ｍｍｏｌ）とピリジン ２．５ｍＬを加え、１０分間攪拌した。この混合溶液を１００℃で１２時間攪拌した。反応溶液を室温まで冷却し、水 ２ｍＬとトルエン ３ｍＬを加えて分液した。有機層を濃縮した残渣をシリカゲルカラムクロマトグラフィー（溶離液 ヘキサン：クロロホルム＝１００：０〜２：１）に通すことにより、２−（４−メトキシフェニル）ピリジン（０．０２３６ｇ、収率２５％）、３−（４−メトキシフェニル）ピリジン（０．０１７７ｇ、収率１９％）、４−（４−メトキシフェニル）ピリジン（０．００７９ｇ、収率８％）をそれぞれ淡黄色固体、淡黄色固体、白色固体として得た。

In a test tube (10 mL) with a screw cap, 0.0047 g (0.025 mmol) of bis (cyclopentadienyl) nickel, 0.0066 g (0.025 mmol) of triphenylphosphine and 0.056 g (0.5 mmol) of potassium tert-butoxide ) Was added, and the inside of the container was replaced with argon. Under an argon atmosphere, 0.063 mL (0.5 mmol) of 4-bromoanisole and 2.5 mL of pyridine were added to the mixture and stirred for 10 minutes. The mixed solution was stirred at 100 ° C. for 12 hours. The reaction solution was cooled to room temperature, and 2 mL of water and 3 mL of toluene were added for liquid separation. The residue obtained by concentrating the organic layer was passed through silica gel column chromatography (eluent hexane: chloroform = 100: 0 to 2: 1) to give 2- (4-methoxyphenyl) pyridine (0.0236 g, yield 25%). , 3- (4-methoxyphenyl) pyridine (0.0177 g, yield 19%) and 4- (4-methoxyphenyl) pyridine (0.0079 g, yield 8%) were respectively pale yellow solid, pale yellow solid, Obtained as a white solid.

2- (4-Methoxyphenyl) pyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.65 (ddd, J = 4.8, 1.7, 1.0 Hz, 1H), 7.95 (md, J = 8.9 Hz, 2H) , 7.73-7.65 (m, 2H), 7.17 (ddd, J = 7.2, 4.8, 1.3 Hz, 1H), 7.00 (md, J = 8.9 Hz, 2H) ), 3.86 (s, 3H).
¹³ C-NMR (CDCl ₃ , ppm): δ 160.4, 157.1, 149.5, 136.6, 132.0, 128.1, 121.4, 119.8, 114.1, 55.3 .
3- (4-Methoxyphenyl) pyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.84 (dd, J = 2.0, 0.5 Hz, 1H), 8.53 (dd, J = 4.8, 1.6 Hz, 1H) 7.81 (ddd, J = 7.9, 2.2, 1.7 Hz, 1H), 7.51 (md, J = 8.8 Hz, 2H), 7.30 (ddd, J = 7.9) , 4.8, 0.7 Hz, 1H), 7.00 (md, J = 8.8 Hz, 2H), 3.85 (s, 3H).
¹³ C-NMR (CDCl ₃ , ppm): δ 159.7, 147.9, 147.7, 136.2, 133.8, 130.1, 128.1, 123.4, 114.5, 55.3 .
4- (4-Methoxyphenyl) pyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.61 (dd, J = 4.6, 1.5 Hz, 2H), 7.59 (md, J = 8.6 Hz, 2H), 7.46 (Dd, J = 4.5, 1.6 Hz, 2H), 7.00 (md, J = 8.8 Hz, 2H), 3.86 (s, 3H).
¹³ C-NMR (CDCl ₃ , ppm): δ 160.5, 150.1, 147.8, 130.3, 128.1, 121.0, 114.5, 55.3.
Example 3

スクリューキャップ付試験管（１０ｍＬ）に、ビス（シクロペンタジエニル）ニッケル ０．００４７ｇ（０．０２５ｍｍｏｌ）、トリフェニルホスフィン ０．００６６ｇ（０．０２５ｍｍｏｌ）、４−ブロモビフェニル ０．１１６６ｇ（０．５ｍｍｏｌ）及びカリウムｔｅｒｔ−ブトキシド ０．０５６ｇ（０．５ｍｍｏｌ）を加え、容器内をアルゴンで置換した。この混合物にアルゴン気流下で、ピリジン ２．５ｍＬを加え、１０分間攪拌した。この混合溶液を１００℃で１２時間攪拌した。反応溶液を室温まで冷却し、水 ２ｍＬとトルエン ３ｍＬを加えて分液した。有機層を濃縮した残渣をシリカゲルカラムクロマトグラフィー（溶離液 ヘキサン：クロロホルム＝１００：０〜２：１）に通すことにより、２−（４−ビフェニリル）ピリジン（０．０４０５ｇ、収率３５％）、３−（４−ビフェニリル）ピリジン（０．０３４６ｇ、収率３０％）、４−（４−ビフェニリル）ピリジン（０．００８４ｇ、収率７％）をそれぞれ淡い茶色固体、淡い茶色固体、黄色固体として得た。

In a test tube with a screw cap (10 mL), 0.0047 g (0.025 mmol) of bis (cyclopentadienyl) nickel, 0.0066 g (0.025 mmol) of triphenylphosphine, 0.1166 g (0.5 mmol) of 4-bromobiphenyl ) And 0.056 g (0.5 mmol) of potassium tert-butoxide were added, and the inside of the container was replaced with argon. Under an argon stream, 2.5 mL of pyridine was added to this mixture and stirred for 10 minutes. The mixed solution was stirred at 100 ° C. for 12 hours. The reaction solution was cooled to room temperature, and 2 mL of water and 3 mL of toluene were added for liquid separation. The residue obtained by concentrating the organic layer was passed through silica gel column chromatography (eluent hexane: chloroform = 100: 0 to 2: 1) to give 2- (4-biphenylyl) pyridine (0.0405 g, yield 35%), 3- (4-biphenylyl) pyridine (0.0346 g, yield 30%) and 4- (4-biphenylyl) pyridine (0.0084 g, yield 7%) as a light brown solid, light brown solid, and yellow solid, respectively. Obtained.

2- (4-Biphenylyl) pyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.72 (d, J = 4.6 Hz, 1H), 8.08 (d, J = 8.4 Hz, 2H), 7.80-7.75 (M, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.66 (d, J = 7.2 Hz, 2H), 7.46 (dd, J = 7.6, 7. 6 Hz, 2H), 7.37 (dd, J = 7.4, 7.4 Hz, 1H), 7.27-7.21 (m, 1H).
¹³ C-NMR (CDCl ₃ , ppm): δ 157.1, 149.8, 141.8, 140.6, 138.3, 136.9, 128.9, 127.6, 127.5, 127.4 , 127.2, 122.2, 120.5.
MS: 231 (M ^<+> ).
3- (4-Biphenylyl) pyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.91 (d, J = 1.8 Hz, 1H), 8.61 (dd, J = 4.8, 1.4 Hz, 1H), 7.93 (Dt, J = 7.9, 1.9 Hz, 1H), 7.72 (d, J = 8.4 Hz, 2H), 7.69-7.62 (m, 4H), 7.47 (dd, J = 7.6, 7.6 Hz, 2H), 7.41-7.37 (m, 2H).
¹³ C-NMR (CDCl ₃ , ppm): δ 148.6, 148.3, 141.1, 140.4, 136.7, 136.3, 134.3, 129.0, 127.9, 127.7 , 127.6, 127.2, 123.7.
MS: 231 (M ^<+> ).
4- (4-Biphenylyl) pyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.68 (d, J = 5.5 Hz, 2H), 7.72 (s, 4H), 7.64 (d, J = 7.3 Hz, 2H) ), 7.56 (d, J = 6.0 Hz, 2H), 7.48 (dd, J = 7.6, 7.6 Hz, 2H), 7.39 (t, J = 7.4 Hz, 1H) .
¹³ C-NMR (CDCl ₃ , ppm): δ 150.2, 148.1, 142.1, 140.3, 136.9, 129.0, 127.9, 127.8, 127.5, 127.2 , 121.6.
MS: 231 (M ^<+> ).
Example 4

スクリューキャップ付試験管（１０ｍＬ）に、ビス（シクロペンタジエニル）ニッケル ０．００４７ｇ（０．０２５ｍｍｏｌ）、トリフェニルホスフィン ０．００６６ｇ（０．０２５ｍｍｏｌ）およびカリウムｔｅｒｔ−ブトキシド ０．０５６ｇ（０．５ｍｍｏｌ）を加え、容器内をアルゴンで置換した。この混合物にアルゴン雰囲気下で、４−ブロモ−ｔｅｒｔ−ブチルベンゼン ０．０８７ｍＬ（０．５ｍｍｏｌ）とピリジン ２．５ｍＬを加え、１０分間攪拌した。この混合溶液を１００℃で１２時間攪拌した。反応溶液を室温まで冷却し、水 ２ｍＬとトルエン ３ｍＬを加えて分液した。有機層を濃縮した残渣をシリカゲルカラムクロマトグラフィー（溶離液 ヘキサン：クロロホルム＝１００：０〜２：１）に通すことにより、２−（４−ｔｅｒｔ−ブチルフェニル）ピリジン（０．０２９２ｇ、収率２８％）、３−（４−ｔｅｒｔ−ブチルフェニル）ピリジン（０．０２２８ｇ、収率２２％）、４−（４−ｔｅｒｔ−ブチルフェニル）ピリジン（０．０１１４ｇ、収率１１％）をそれぞれ無色透明液体、黄色固体、白色固体として得た。

In a test tube (10 mL) with a screw cap, 0.0047 g (0.025 mmol) of bis (cyclopentadienyl) nickel, 0.0066 g (0.025 mmol) of triphenylphosphine and 0.056 g (0.5 mmol) of potassium tert-butoxide ) Was added, and the inside of the container was replaced with argon. Under an argon atmosphere, 0.087 mL (0.5 mmol) of 4-bromo-tert-butylbenzene and 2.5 mL of pyridine were added to the mixture and stirred for 10 minutes. The mixed solution was stirred at 100 ° C. for 12 hours. The reaction solution was cooled to room temperature, and 2 mL of water and 3 mL of toluene were added for liquid separation. The residue obtained by concentrating the organic layer was passed through silica gel column chromatography (eluent hexane: chloroform = 100: 0 to 2: 1) to give 2- (4-tert-butylphenyl) pyridine (0.0292 g, yield 28). %), 3- (4-tert-butylphenyl) pyridine (0.0228 g, yield 22%) and 4- (4-tert-butylphenyl) pyridine (0.0114 g, yield 11%) were each colorless and transparent. Obtained as a liquid, yellow solid, white solid.

2- (4-tert-Butylphenyl) pyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.66 (td, J = 4.8, 1.4 Hz, 1H), 7.92 (md, J = 8.6 Hz, 2H), 7.72 −7.67 (m, 2H), 7.49 (md, J = 8.6 Hz, 2H), 7.17 (ddd, J = 8.9, 8.9, 4.6 Hz, 1H), 1. 35 (brs, 9H).
¹³ C-NMR (CDCl ₃ , ppm): δ 157.4, 152.0, 149.5, 136.6, 136.5, 126.5, 125.6, 121.7, 120.2, 34.6 31.2.
MS: 211 (M ^<+> ).
3- (4-tert-butylphenyl) pyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.85 (dd, J = 2.6, 0.7 Hz, 1H), 8.56 (dd, J = 4.8, 1.6 Hz, 1H) 7.86 (ddd, J = 7.9, 2.3, 1.7 Hz, 1H), 7.55-7.48 (m, 4H), 7.33 (ddd, J = 7.9, 4 .8, 0.8 Hz, 1H), 1.36 (brs, 9H).
¹³ C-NMR (CDCl ₃ , ppm): δ 151.2, 148.14, 148.1, 136.4, 134.8, 134.1, 126.7, 126.0, 123.5, 34.5 31.2.
MS: 211 (M ^<+> ).
4- (4-tert-butylphenyl) pyridine
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 8.63 (d, J = 6.2 Hz, 2H), 7.59 (d, J = 8.5 Hz, 2H), 7.51 (d, J = 8.5 Hz, 2H), 7.50 (d, J = 8.5 Hz, 2H), 1.37 (brs, 9H).
¹³ C-NMR (CDCl ₃ , ppm): δ 152.4, 150.1, 148.1, 135.1, 126.6, 126.0, 121.4, 34.7, 31.2.
MS: 211 (M ⁺ )

Claims (1)

Ar-X (1) in the presence of potassium tert-butoxide, triphenylphosphine and bis (cyclopentadienyl) nickel
(In the formula, Ar represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group or naphthyl group optionally substituted with a phenyl group, and X represents iodine, bromine or Indicates chlorine.)
A process for producing arylpyridines, characterized by reacting an aryl halide represented by general formula (II) with pyridine.