JP5924984B2 - Trifluoromethylpyridinone compound and method for producing the same - Google Patents

Description

  The present invention relates to a novel pyridinone compound having a trifluoromethyl group.

  It is well known that introduction of a trifluoromethyl group into a medical pesticide or a functional material contributes to an improvement in physiological activity or material properties.

  Various trifluoromethylation methods have been reported in the past, but most of them were applicable only to heterocyclic or aromatic ring compounds having an excess of π electrons. However, it is a well-known fact that π-electron deficient heteroaromatic compounds play an important role in medical pesticides and functional materials, and a simple and efficient method for introducing a trifluoromethyl group into such compounds is known. Developing was an important issue.

  In Patent Document 1, it is reported that a pyridinone ring having a trifluoromethyl group works as a positive allosteric factor of a metabotropic receptor subtype and is useful for prevention of central nervous system disorders such as anxiety and schizophrenia. ing. However, it is limited to pyridinone compounds that are other than hydrogen atoms at the 4-position and have a trifluoromethyl group at the 3-position, and react with a copper salt and methyl 2,2-difluoro-2-fluorosulfonyl acetate on pyridinone iodide. In this way, the trifluoromethyl group is introduced.

  For example, in Non-Patent Document 1, an amino group of 2-amino-3- (trifluoromethyl) pyridine is converted to a hydroxy group by providing sodium nitrite in an aqueous sulfuric acid solution, thereby converting 3- (trifluoromethyl) pyridine. -2 (1H) -one is disclosed to be obtained in 69% yield. In Patent Document 2, the chloro group of 2-chloro-3- (trifluoromethyl) pyridine is converted into a hydroxy group by refluxing in acetic acid for 7 days to give 3- (trifluoromethyl) pyridine-2 (1H ) -One was disclosed to be obtained in 93% yield (20 pages, 0057 paragraph). However, this method has a problem that the reaction time takes 7 days. Furthermore, it was necessary to obtain a trifluoromethylated raw material.

  Patent Document 3 is excellent in that a trifluoromethyl group is directly introduced into pyridin-2 (1H) -one using a Fenton reagent and the substrate reacts even if it has an unprotected NH group. However, the yield is about 50% (ex. 11). In this method, a trifluoromethyl group can be introduced only at the 3-position.

  In Patent Document 4, the chloro group of 2-chloro-5- (trifluoromethyl) pyridine is converted to a hydroxy group by refluxing in acetic acid for 45 hours in the presence of silver acetate to convert 5- (trifluoromethyl) pyridine-2 ( It is disclosed that 1H) -one was obtained in 51% yield (Step C of Ex. 111). The problem was that a reaction at a high temperature of 140 ° C. was required and a reaction time of 45 hours was required. Furthermore, it was necessary to obtain a trifluoromethylated raw material.

  Patent document 5 discloses that 5- (trifluoromethyl) pyridin-2 (1H) -one can be obtained by allowing sulfur tetrafluoride to act on 5- (carboxy) pyridin-2 (1H) -one. However, sulfur tetrafluoride is toxic and not versatile.

  In Non-Patent Document 2, 5- (trifluoromethyl) pyran- (2H) -one is subjected to hexamethyldisilazane and DBU and stirred for 3 days to give 5- (trifluoromethyl) pyridine-2 in a yield of 16%. Although it discloses that (1H) -one is obtained, the yield is low.

  Non-Patent Document 3 discloses a method for introducing a trifluoromethyl group into a pyridine ring, but there is no example applied to a pyridinone compound.

International Publication No. 2009-0033702 International Publication No. 2007-126765 JP 2008-137993 A U.S. Pat. No. 4,038,396 U.S. Pat. No. 4,230,864

J. Fluorine Chem. 1999, 93, 153 Synthesis 1991, 883 Eur. J. Org. Chem. 2003, 1559

  Π-electron deficient heteroaromatic compounds are known to play an important role in medical pesticides and functional materials, and developing a simple and efficient method for introducing a trifluoromethyl group into the compound It was an important issue. The present invention provides a novel pyridinone compound having a trifluoromethyl group as an excellent pharmaceutical and agrochemical intermediate pyridinone compound.

  As a result of intensive studies, the present inventors have found a novel pyridinone compound having a trifluoromethyl group, and by using an iodinated pyridinone compound, copper halide, (trifluoromethyl) trimethylsilane and salts, We found that it can be synthesized efficiently.

That is, the present invention relates to a trifluoromethylpyridinone compound represented by the following formulas (1) to (7).
(1) A trifluoromethylpyridinone compound having a trifluoromethyl group, which is represented by the following formulas (1) to (7).

(2) From the group consisting of a pyridinone iodide compound represented by the following formulas (8) to (13), copper halide, (trifluoromethyl) trimethylsilane and potassium chlorofluoride, cesium fluoride and tert-butoxypotassium A method for producing a trifluoromethylpyridinone compound represented by formulas (1) to (7) according to (1), wherein at least one selected salt is reacted.

  The inventors have found a novel pyridinone compound having a trifluoromethyl group, and have found that the pyridinone compound can be synthesized by a reaction using an iodinated pyridinone compound, copper halide, (trifluoromethyl) trimethylsilane and salts.

  The pyridinone compound having a trifluoromethyl group of the present invention is an excellent intermediate for medical and agricultural chemicals and a functional material, and is industrially useful. The present invention provides a novel pyridinone compound having a trifluoromethyl group represented by the above formulas (1) to (7).

  The present invention relates to a novel pyridinone compound having a trifluoromethyl group represented by formula (1) to formula (7), and the pyridinone compound represented by formula (8) to formula (13). It is synthesized by a reaction of substituting the iodine atom with a trifluoromethyl group, that is, a reaction using an iodinated pyridinone compound, copper halide, (trifluoromethyl) trimethylsilane and salts.

  The iodinated pyridinone compound includes a 1-substituted pyridin-2-one skeleton substituted at the 1-position with a methyl group or a paramethoxybenzyl group, and at least one of carbons constituting the pyridin-2-one skeleton is It may be bonded to an iodine atom, but 5-iodo-1- (p-methoxybenzyl) pyridin-2-one, 3-iodo-1-methylpyridin-2-one, 3,5-diiodo-1- Methylpyridin-2-one, 3-iodo-1-methyl-5,6,7,8-tetrahydroquinolin-2-one, 3-iodo-1-methyl-1,5,6,7-tetrahydrocyclo Penta [b] pyridin-2-one, 5,6-dihydro-3-iodo-1- (p-methoxybenzyl) -benzo [h] quinolin-2-one are preferred.

  The trifluoromethylpyridinone compounds represented by the above formulas (1) and (2) are iodinated pyridinone compounds, each of which is 5-iodo-1- (p-methoxybenzyl) represented by the above formula (8). From pyridine-2-one and 3-iodo-1-methylpyridin-2-one represented by the above formula (9), trifluoromethylpyridinone compounds represented by the above formula (3) and formula (4) are And a trifluoromethylpyridinone iodide compound from 3,5-diiodo-1-methylpyridin-2-one represented by the formula (10) and the formulas (5) to (7). The dinone compound is an iodinated pyridinone compound, which is 3-iodo-1-methyl-5,6,7,8-tetrahydroquinolin-2-one represented by the formula (11), respectively. 3-Iodo-1-methyl-1,5,6,7-tetrahydrocyclopenta [b] pyridin-2-one represented by formula (12), 5,6- represented by formula (13) It is produced from dihydro-3-iodo-1- (p-methoxybenzyl) -benzo [h] quinolin-2-one by the reaction of the present invention in which the iodine atom is substituted with a trifluoromethyl group.

  As the copper halide that can be used in the present invention, copper (I) chloride, copper (I) bromide, and copper (I) iodide are preferable, and the target product can be obtained in a high yield. I) is more preferred.

  The salts used in the present invention are at least one compound selected from the group consisting of potassium fluoride, cesium fluoride and tert-butoxypotassium. As potassium fluoride, cesium fluoride, and tert-butoxy potassium, commercially available potassium fluoride, cesium fluoride, and tert-butoxy potassium can be directly used. It can be used even in a dissolved state. The potassium fluoride includes potassium fluoride produced by a spray-drying method with a fine powder and a large specific surface area in terms of dissolution and dispersibility in a reaction organic solvent.

  The solvent used in the present invention is preferably an aprotic polar solvent. Among aprotic polar solvents, N, N-dimethylformamide, N-methylpyrrolidone, N, N-dimethylpropyleneurea, N, N-dimethylethyleneurea, dimethylsulfoxide, hexamethylphosphoric triamide, N, N- Dimethylacetamide is preferable, and these can be used alone or in combination of two or more. Among these, N, N-dimethylformamide is particularly preferable because it is easily available and the target product can be obtained in high yield.

  In the reaction of the present invention, the reaction temperature is preferably from 0 ° C. to the boiling point of the solvent, more preferably from 20 ° C. to 90 ° C.

  The amount of the reagent used in the present invention is preferably 1 to 100 moles, more preferably 1 to 10 moles of (trifluoromethyl) trimethylsilane with respect to 1 mole of the pyridinone iodide compound. 1-100 mol is preferable with respect to 1 mol of iodinated pyridinone compounds, and, as for copper halide, 1-10 mol is more preferable. 1-100 mol is preferable with respect to 1 mol of iodide pyridinone compounds, and, as for potassium fluoride or tert- butoxy potassium, 1-10 mol is more preferable. Although the amount of the solvent is not particularly limited, 1 to 100 mL of solvent is preferable and 1 to 20 mL is more preferable with respect to 1 g of the pyridinone iodide compound.

  The reagent used in the present invention can be introduced according to any conventional method, and it is preferable to first mix the solvent, copper halide, salts and substrate, and finally provide (trifluoromethyl) trimethylsilane.

  In the reaction for replacing the iodine atom in the pyridinone iodide compound of the present invention with a trifluoromethyl group, the reactor can be either an open-air reactor or a sealed reactor such as an autoclave. The reaction pressure can be either atmospheric pressure or pressurized.

  The trifluoromethylpyridinone compound obtained by the trifluoromethylation reaction of the iodinated pyridinone compound can be isolated and purified from the reaction solution by a general method. For example, the reaction solution is washed with water, solvent extracted, dried, After concentration, examples thereof include distillation purification, column chromatography using an adsorbent such as silica gel and alumina, salting out, crystallization, recrystallization and the like, and trifluoromethylpyridinone which is the target compound of the present invention A compound can be obtained.

  In the purification by column chromatography, for example, hexane / ethyl acetate (0/100 to 100/0 (v / v)) can be used as the developing solvent. As the mixing ratio when using a mixed solvent of hexane and ethyl acetate, a mixed solvent at an arbitrary volume ratio (v / v) can be used, but the target product can be easily isolated in a high yield. Since it is obtained, 50/1 to 1/1 (v / v) is preferable.

The trifluoromethylpyridinone compound of the present invention thus obtained can be obtained by ¹ H NMR, ¹³ C NMR, ¹⁹ F NMR, infrared absorption spectroscopy (IR), elemental analysis, gas chromatography (GC), etc. The structure can be specified.

  Next, the present invention will be described in detail, but the present invention is not limited thereto.

  As an analytical instrument, NMR measurement is JNM-AL300 manufactured by JEOL Ltd., IR measurement is FT / IR-4100 manufactured by JASCO Corporation, and melting point measurement is melting point measuring instrument MP- manufactured by Yamato Scientific Co., Ltd. 21. Elemental analysis was performed using a Perkin-Elmer CHNS / O Analyzer 2400.

Production Example 1 (raw material synthesis)
5-Iodopyridin-2-one (0.44 g, 2.0 mmol), potassium carbonate (0.30 g, 2.2 mmol) and p-methoxybenzyl chloride (0.31 g, 2.0 mmol) were mixed with N, N-dimethyl. Stir overnight at 25 degrees in 10 mL formamide. 20 mL of water was added to the reaction mixture, followed by extraction with ethyl acetate (20 mL × 3 times). The ethyl acetate layer was washed with water (20 mL × 3 times) and then dried over anhydrous magnesium sulfate. The solvent was distilled off after filtration of the dehydrating agent, and silica gel column chromatography (filler: Kanto Chemical Co., Ltd. silica gel 60 spheres (particle size 63-210 mm), developing solvent hexane: ethyl acetate = 2: 1 to 1: 1 (v: v) ). 0.56 g (yield 82%) of 5-iodo-1- (p-methoxybenzyl) pyridin-2-one was obtained as a yellow oil.

Example 1 Synthesis of Compound of Formula (1) Potassium fluoride (0.15 g, 2.6 mmol) and copper iodide (0.50 g, 2.6 mmol) and 5-iodo-1- (p-methoxybenzyl) pyridine- 2-one (0.34 g, 1.0 mmol) was homogenized with 5 ml of N, N-dimethylformamide, followed by the addition of (trifluoromethyl) trimethylsilane (0.38 mL, 2.6 mmol). The reaction solution was stirred at 80 ° C. for 6 hours. After diluting with 10 mL of aqueous ammonium chloride solution, the mixture was extracted with ethyl acetate (20 mL × 3 times). After the ethyl acetate layer was dried over anhydrous magnesium sulfate, the solvent was distilled off, and silica gel chromatography (filler, silica gel 60 spherical 63-210 mm, manufactured by Kanto Chemical Co., Inc., developing solvent hexane: ethyl acetate = 4: 1 to 1: 1 ( v: Purified in v)). 0.19 g of 5-trifluoromethyl-1- (p-methoxybenzyl) pyridin-2-one of the formula (1) was obtained as a white solid (yield 68%).
Mp: 48-49 ° C (Mp represents melting point; the same applies hereinafter)
¹ H NMR (300 MHz, CDCl ₃ ): δ3.81 (s, 3H), 5.01 (s, 2H), 6.65 (d, J = 9.6 Hz, 1H), 6.90 (m, 2H), 7.27 (m, 2H), 7.42 (dd, J = 9.6, 2.7 Hz, 1H), 7.63 (m, 1H).
¹³ C NMR (75 Hz, CDCl ₃ ): δ52.0, 55.1, 109.6 (q, J = 34.8 Hz), 114.3, 121.4, 123.2 (q, J = 266.6 Hz), 127.1, 129.8, 134.8 (q, J = 1.8 Hz), 136.5 (q, J = 5.0 Hz), 159.7, 161.8.
¹⁹ F NMR (282 Hz, CDCl ₃ ): δ-63.68 (s).
IR (neat, cm ^-1 ): ν3008, 2959, 2840, 1677, 1623, 1514, 1331, 1251, 1167, 1150, 1127.
Anal. Calcd for C ₁₄ H ₁₂ F ₃ NO ₂ : C, 59.37; H, 4.27; N, 4.95. Found: C, 58.93; H, 4.36; N, 4.90.

Example 2
Except that the copper (I) iodide was replaced with copper (I) bromide, the same conditions as in Example 1 were applied. As a result, 5-trifluoromethyl-1- (p-methoxybenzyl) pyridine of formula (1) 2-one was obtained in 30% yield.

Example 3
Except that the copper (I) iodide was replaced with copper (I) chloride, the same conditions as in Example 1 were applied. As a result, 5-trifluoromethyl-1- (p-methoxybenzyl) pyridine-2 represented by the formula (1) was obtained. -On was obtained in 29% yield.

Example 4
Except that potassium fluoride was replaced with tert-butoxypotassium, the same conditions as in Example 1 were applied. As a result, 5-trifluoromethyl-1- (p-methoxybenzyl) pyridin-2-one of formula (1) was recovered. Obtained at a rate of 70%.

Example 5
Except for replacing potassium fluoride with cesium fluoride, the same conditions as in Example 1 were applied. As a result, 5-trifluoromethyl-1- (p-methoxybenzyl) pyridin-2-one of formula (1) was obtained in a yield. Obtained at 82%.

Example 6 Synthesis of Compound of Formula (2) When 3-iodo-1-methylpyridin-2-one was used as a substrate under the same conditions as in Example 1, 3- (trifluoro) of formula (2) was used. Methyl) -1-methylpyridin-2-one was obtained as a white solid (87% yield).
Mp: 93-94 ° C.
¹ H NMR (300 MHz, CDCl ₃ ): δ3.62 (s, 3H), 6.25 (t, J = 7.2 Hz, 1H), 7.55 (d, J = 6.9 Hz, 1H), 7.76 (d, J = (6.9 Hz, 1H).
¹³ C NMR (75 Hz, CDCl ₃ ): δ37.6, 103.8, 119.9 (q, J = 31.0 Hz), 122.7 (q, J = 271.0 Hz), 138.8 (q, J = 5.0 Hz), 142.4, 158.7 .
¹⁹ F NMR (282 Hz, CDCl ₃ ): δ67.35 (s).
IR (KBr, cm ^-1 ): ν3087, 3053, 3013, 1650, 1569, 1467, 1316, 1126, 1079, 880, 771. Anal.Calcd for C ₇ H ₆ F ₃ NO: C, 47.47; H, 3.41 ; N, 7.91. Found: C, 47.52; H, 3.18; N, 7.88.

Example 7 Synthesis of compound of formula (3) and compound of formula (4) In a reaction vessel purged with argon, potassium fluoride (0.15 g, 2.6 mmol) and copper iodide (0.50 g, 2.6 mmol) and 3,5-Diiodo-1-methylpyridin-2-one (0.18 g, 0.5 mmol) was homogenized with 5 ml of N, N-dimethylformamide followed by (trifluoromethyl) trimethylsilane (0.38 mL, 2.6 mmol) was added. The reaction solution was stirred at room temperature for 48 hours. After diluting with 10 mL of an aqueous ammonium chloride solution, extraction was performed with ethyl acetate (10 mL × 3 times). After the ethyl acetate layer was dried over anhydrous magnesium sulfate, the solvent was distilled off, and silica gel chromatography (filler, silica gel 60 spherical 63-210 mm, manufactured by Kanto Chemical Co., Inc., developing solvent hexane: ethyl acetate = 8: 1 to 2: 1 ( v: Purified in v)). 1-methyl-3,5-bis (trifluoromethyl) pyridin-2-one of formula (3) was converted to white solid (35% yield) and 5-iodo-1-methyl-3- ( Trifluoromethyl) pyridin-2-one was obtained as a white solid (57% yield), respectively.

[Formula (3) compound data]
Mp: 76-77 ° C.
¹ H NMR (300 MHz, CDCl ₃ ): δ3.66 (s, 3H), 7.89 (s, 1H), 7.92 (s, 1H).
¹³ C NMR (75 Hz, CDCl ₃ ): δ38.4, 107.9 (q, J = 32.0 Hz), 120.7 (q, J = 31.0 Hz), 121.9 (q, J = 271.0 Hz), 122.6 (q, J = 269.8 Hz), 134.9 (m), 141.6 (q, J = 5.0 Hz), 158.0.
¹⁹ F NMR (282 Hz, CDCl ₃ ): δ62.84 (s), 67.27 (s).
IR (KBr, cm ^-1 ): ν3054, 1636, 1580, 1505, 1417, 1303, 1207, 1117, 892, 752, 686.
Anal. Calcd for C ₈ H ₅ F ₆ NO: C, 39.20; H, 2.06; N, 5.71. Found: C, 38.72; H, 1.99; N, 5.64.

[Formula (4) compound data]
Mp: 135-136 ° C.
¹ H NMR (300 MHz, CDCl ₃ ): δ3.59 (s, 3H), 7.77 (s, 1H), 7.84 (s, 1H).
¹³ C NMR (75 Hz, CDCl ₃ ): δ37.7, 60.7, 121.6 (q, J = 272.3 Hz), 121.7 (q, J = 31.0 Hz), 146.1 (q, J = 5.0 Hz), 147.2, 157.3 .
¹⁹ F NMR (282 Hz, CDCl ₃ ): δ67.41 (s).
IR (KBr, cm ^-1 ): ν 3046, 1660, 1593, 1556, 1422, 1303, 1175, 1129, 919, 679.
Anal.Calcd for C ₇ H ₅ F ₃ INO: C, 27.75; H, 1.66; N, 4.62. Found: C, 27.66; H, 1.74; N, 4.48.

Example 8 Synthesis of compound of formula (5) The same conditions as in Example 1 were used except that 3-iodo-1-methyl-5,6,7,8-tetrahydroquinolin-2-one was used as the substrate. 1-methyl-3-trifluoromethyl-5,6,7,8-tetrahydroquinolin-2-one of formula (5) was obtained as a white solid (yield 98%).
Mp: 111-112 ° C.
¹ H NMR (300 MHz, CDCl ₃ ): δ1.75 (m, 2H), 1.89 (m, 2H), 2.56 (t, J = 6.0 Hz, 2H), 2.68 (t, J = 5.7 Hz, 2H) , 3.53 (s, 3H), 7.48 (s, 1H).
¹³ C NMR (75 Hz, CDCl ₃ ): δ21.2, 21.8, 27.0, 27.6, 30.0, 116.1 (q, J = 30.4 Hz), 123.0 (q, J = 270.4 Hz), 139.6 (q, J = 5.0 Hz), 148.6, 158.7.
¹⁹ F NMR (282 Hz, CDCl ₃ ): δ66.92 (s).
IR (KBr, cm ^-1 ): ν 3037, 2948, 2874, 1666, 1606, 1557, 1427, 1323, 1174, 1133, 1100, 1071, 983, 944.
Anal. Calcd for C ₁₁ H ₁₂ F ₃ NO: C, 57.14; H, 5.23; N, 6.06. Found: C, 57.20; H, 4.99; N, 6.07.

Example 9 Synthesis of Compound of Formula (6) Same as Example 1 except that 3-iodo-1-methyl-1,5,6,7-tetrahydrocyclopenta [b] pyridin-2-one was used as the substrate. When subjected to conditions, 1-methyl-3- (trifluoromethyl) -1,5,6,7-tetrahydrocyclopenta [b] pyridin-2-one of formula (6) was obtained as a white solid ( Yield 99%).
Mp: 143-144 ° C.
¹ H NMR (300 MHz, CDCl ₃ ): δ2.20 (quint., J = 7.5 Hz, 2H), 2.83 (t, J = 7.5 Hz, 2H), 2.97 (m, 2H), 3.54 (s, 3H ), 7.65 (s, 1H).
¹³ C NMR (75 Hz, CDCl ₃ ): δ22.2, 29.8, 32.5, 115.8 (q, J = 29.2 Hz), 116.9, 123.2 (q, J = 271.0 Hz), 135.4 (q, J = 5.0 Hz) , 155.4, 159.2.
¹⁹ F NMR (282 Hz, CDCl ₃ ): δ66.97 (s).
IR (KBr, cm ^-1 ): ν3021, 2918, 2864, 1642, 1577, 1530, 1433, 1231, 791, 753.
Anal. Calcd for C ₁₀ H ₁₀ F ₃ NO: C, 55.30; H, 4.64; N, 6.45. Found: C, 55.00; H, 4.43; N, 5.96.

Example 10 Synthesis of Compound of Formula (7) Same as Example 1 except that 5,6-dihydro-3-iodo-1- (p-methoxybenzyl) -benzo [h] quinolin-2-one was used as the substrate. When subjected to conditions, 5,6-dihydro-1- (p-methoxybenzyl) -3- (trifluoromethyl) benzo [h] quinolin-2-one of formula (7) was obtained as a highly viscous yellow oil. (Yield 98%).
¹ H NMR (300 MHz, CDCl ₃ ): δ2.92 (m, 4H), 3.80 (s, 3H), 5.57 (s, 2H), 6.90 (d, J = 8.7 Hz, 2H), 7.25 (m, 1H), 7.36 (m, 2H), 7.45 (d, J = 8.7 Hz, 2H), 7.68 (s, 1H), 8.27 (m, 1H).
¹³ C NMR (75 Hz, CDCl ₃ ): δ26.5, 27.9, 55.1, 67.4, 111.1 (q, J = 32.2 Hz), 113.7, 123.3 (q, J = 271.0 Hz), 123.5, 125.4, 127.0, 127.9 , 129.1, 129.2, 129.3, 133.4, 136.3 (q, J = 4.4 Hz), 138.5, 152.8, 158.8 (q, J = 1.9 Hz).
¹⁹ F NMR (282 Hz, CDCl ₃ ): δ64.21 (s).
IR (KBr, cm ^-1 ): ν3008, 2940, 2839, 1614, 1515, 1439, 1304, 1274, 1248, 1135, 1078.
Anal. Calcd for C ₂₂ H ₁₈ F ₃ NO ₂ : C, 68.57; H, 4.71; N, 3.63. Found: C, 68.39; H, 4.78; N, 3.54.

  This invention discovered the pyridinone compound which has a novel trifluoromethyl group, and also discovered that it can synthesize | combine by using an iodinated pyridinone compound, copper halide, salts, and (trifluoromethyl) trimethylsilane. . Pyridinone compounds having a trifluoromethyl group are excellent raw materials for medical and agrochemical intermediates and functional materials, and the present invention provides a novel trifluoromethylpyridinone compound that can be synthesized simply and efficiently. Is also useful.

Claims (2)

A pyridinone compound having a trifluoromethyl group, which is represented by the following formulas (3) to (7).
A method for producing a trifluoromethylpyridinone compound represented by the following formulas (1) to (7),

At least selected from the group consisting of a pyridinone iodide compound represented by the following formulas (8) to (13), copper halide, (trifluoromethyl) trimethylsilane, and potassium fluoride, cesium fluoride and tert-butoxypotassium. A method for producing a trifluoromethylpyridinone compound represented by the above formulas (1) to (7), wherein one kind of salt is reacted.