Pyridine-derivatives

Electric Literature of 67367-26-4 ,Some common heterocyclic compound, 67367-26-4, molecular formula is C8H9NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

In a 250 mL dry round bottom flask with a reflux condenser and magnetic stirrer was placed with 2-chloro-3-ethyl nicotinate (12.0 g, 64.7 mmol) in dry methanol (200 mL), and CH3ONa (21 mL, 97.0 mmol, 25% in methanol) were added slowly and the reaction mixture was refluxed for 16 hour. The reaction mixture was cooled to room temperature and quenched by addition of a saturated aqueous NH4CI solution and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give 2-methoxy-3-methyl nicotinate (10.0 g, 93%). In a dry 500 mL round bottom flask NaH (549 mg, 13.7 mmol, 60% in mineral oil) was added in DMF (10 mL). Acetophenone (1.5 g, 12.5 mmol) in dry DMF (10 mL) was added drop-wise at O0C in 30 min. The reaction mixture was stirred for 1 h at room temperature. 2- Methoxy-3-m ethyl nicotinate (2.08 g, 12.5 mmol) dissolved into dry DMF (10 mL) was added slowly on cooling. After addition the mixture was stirred for 16 h at EPO room temperature. The reaction mixture was quenched by addition of a saturated aqueous NH4CI solution and diluted with water. The solid was filtered off, washed with water and dried to give the diketo product (2.94 g, 92%). Poly phosphoric acid (15.0 g) was heated at 9O0C and the diketo compound (1.5 g, 3.50 mmol) was added slowly and heated at 9O0C for 1 hours. The reaction mixture was cooled to room temperature and diluted with water. The solid was separated by filtration, washed with water and dried to give pure 2-phenyl-4H-pyrano[2,3- b]pyridin-4-one (655 mg, 50%); MS (ES) m/z: 224.94 (M+1 ), 223.95 (M); MP 103- 1050C

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67367-26-4, its application will become more common.

Reference:
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20260-53-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 20260-53-1, name is Nicotinoyl chloride hydrochloride. A new synthetic method of this compound is introduced below.

To a solution of 1 (50 mg, 0.071 mmol) in 354 ml of pyridine at room temperature was added nicotinoyl chloride hydrochloride (15 mg, 0.085 mmol) followed by triethylamine (23 ml, 0.170 mmol). After stirring for 1.5 h, 4-dimethylamino pyridine (8.6 mg, 0.071 mmol) was added. After stirring 5 h, additional triethylamine (23 ml, 0.170 mmol), 4-dimethylamino pyridine (8.6 mg, 0.071 mmol), and nicotinoyl chloride hydrochloride (15 mg, 0.085 mmol) was added along with a 50 ml pyridine rinse. After stirring 18 h the reaction was treated with 0.5 ml of saturated aqueous sodium bicarbonate and washed with methylene chloride (4×1 ml). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to a light brown oil. Chromatography (14 g of flash silica gel), eluting with ethyl acetate-hexanes (10:1) provided 49 mg (85%) of the free base as a white foam. The nicotinoate was dissolved in 1 ml of methylene chloride and treated with a 1.0 M solution of hydrogen chloride in diethyl ether (90 ml, 0.090 mmol). The clear, colorless solution was allowed to stand at room temperature for 5 min. Removal of the solvent in vacuo produced 51 mg of the title compound as a white foam: 500 MHz 1H NMR (CDCl3) d 8.94 (s, 1H), 8.78 (br s, 1H), 8.29 (d, 1H, J=7.0 Hz), 7.57 (br s, 1H), 7.38 (d, 2H, J=7.1 Hz), 7.30-7.16 (m, 5H), 7.10 (dd, 1H, J=8.4, 1.7 Hz), 6.88 (d, 1H, J=8.4 Hz), 6.71 (m, 1H), 5.80 (d, 1H, J=15 Hz), 5.74 (d, 1H, J=9.6 Hz), 5.56 (br s, 1H), 5.00 (d, 1H, J=9.6 Hz), 4.95 (t, 1H, J=8.9 Hz), 4.84 (d, 1H, J=9.8 Hz), 4.77-4.72 (m, 1H), 3.91 (s, 3H), 3.39 (dd, 1H, J=13, 8.2 Hz), 3.23-3.14 (m, 2H), 3.06 (dd, 1H, J=14, 7.6 Hz), 2.81-2.74 (m, 1H), 2.62-2.45 (m, 2H), 1.93 (ddd, 1H, J=14, 12, 4.8 Hz), 1.78-1.70 (m, 1H), 1.66-1.59 (m, 1H), 1.25 (s, 3H), 1.20 (d, 3H, J=7.0 Hz), 1.19 (s, 3H), 0.98 (d, 3H, J=6.7 Hz), 0.84 (d, 3H, J=6.5 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20260-53-1, Nicotinoyl chloride hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; Wayne State University; University of Hawaii; US6680311; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 72811-73-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 72811-73-5, name is 4-(m-Tolylamino)pyridine-3-sulfonamide. This compound has unique chemical properties. The synthetic route is as follows.

Example 12; Preparation of torsemide [1]; A mixture of 4-m-tolylamino-3-pyridinesulfonamide [2], yellow powder with 98.0 % purity (0.5 % of 4-chloro-3-pyridinesulfonamide [4]) by HPLC (5.0 g, 19 mmol), 1 N aqueous solution of sodium hydroxide (19 mL, 19 mmol) and phenyl isopropylcarbamate (5.1 g, 23 mmol) was stirred at 90-100 C for 5 hours diluted with water (20 mL), cooled to 20-25 C, extracted with ter-butyl methyl ether (4 x 30 mL), neutralized with an 1 N aqueous solution of sulfuric acid at 20-25 C and stirred for 1 hour at 60-70 C. The precipitated solids were filtered off, washed on filter with hot water (20 mL) and acetone (20 mL) to give 5.6 g (85 %) of crude torsemide [1] 99.4 % purity (0.1 % of 4-m-tolylamino-3-pyridinesulfonamide [2]) by HPLC. A solution of sodium hydroxide (0.62 g, 16 mmol) in water (15 g) was added to a stirred suspension of crude torsemide [1] (5.0 g, 14 mmol) in water (45 g) at 20-30 C. The mixture was stirred at 20-30 C until a complete dissolution of the solids (pH 12.9) and charcoal SA (0.5 g) was added to the solution. After stirring for 2 hours, the obtained mixture was filtered off, cooled to 15-20 C and acidified to pH 4.6 with a 1 N solution of sulfuric acid in water (-28 mL, 28 mmol) at the same temperature. The obtained suspension was stirred for about 2 hours at 15-20 C and filtered. The solid was washed on the filter with water (50 g) and dried under reduced pressure at 55 i 5 C (water bath) to a constant weight to give 4.7 g of torsemide [1] as a white solid with 99.4 % purity by HPLC.

According to the analysis of related databases, 72811-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FINETECH LABORATORIES LTD.; WO2003/97603; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)pyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Safety of 2,3-Dichloro-5-(trifluoromethyl)pyridine, blongs to pyridine-derivatives compound. Safety of 2,3-Dichloro-5-(trifluoromethyl)pyridine

Example 6 : Preparation of 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-1-phenylethanamine; Preparation of 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl-1-phenylethanone; To a suspension of 2.6 g (0.065 mol) of sodium hydride 60% in dimethoxyethane at room temperature is added 3.4 mL (0.029 mol) of acetophenone. After 45 min. , 5.55 mL ( 0.038 mol) of 2,3-dichloro-5-(trifluoromethyl)pyridine is added. After 25 min., the reaction mixture is poured over 100mL of hydrochloric acid 1N, extracted twice with 100mL of ethyl acetate. The organic phase is washed twice 100 mL of water, dried over magnesium sulfate, filtered and concentrated to provide 15g of crude material which is purified over a column of silica by using a mixture of heptane and ethyl acetate as eluent, to yield to 5.74 g of desired product 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-1-phenylethanone (74%). RMN 1H delta (ppm) 8,73 ; (1H, s) ; 7,95 (1H, s) ; 7,45 (2H, m) ; 7,42 (2H, m) ; 4,75 (2H, s).

The synthetic route of 69045-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer CropScience S.A.; EP1548007; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4487-59-6, name is 2-Bromo-5-nitropyridine, the common compound, a new synthetic route is introduced below. SDS of cas: 4487-59-6

-Bromo-5-nitropyridine (0.3 g, 1.48 mmol) was treated with piperazine (0.64 g, 7.89 mmol) in tetrahydrofuran (4 mL) and the reaction mixture was stirred for 30 minutes. Subsequently the reaction mixture was poured onto ice-cold water (25 mL) and extracted with ethyl acetate (25 mL). The organic layer was washed with brine and evaporated to furnish the product.

The synthetic route of 4487-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORCHID RESEARCH LABORATORIES LIMITED.; US2007/167413; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1227177-68-5, name is 3-Cyclopropyl-2-fluoropyridine. A new synthetic method of this compound is introduced below., Quality Control of 3-Cyclopropyl-2-fluoropyridine

STEP 3. N-(4-(3-CYCLOPROPYLPYRIDIN-2-YLOXY)PHENYL)BENZO[D]THIAZOL-2-AMINE To a solution of 4-(benzo[d]thiazol-2-ylamino)phenol (1.17 g, 4.81 mmol) in DMSO (40 mL) was added cesium carbonate (1.88 g, 5.78 mmol) and 3-cyclopropyl-2-fluoropyridine (660 mg, 4.81 mmol). The resulting mixture was heated to 125 C. for 16 h. After cooling to RT, the reaction mixture was diluted with EtOAc and washed with water and brine several times to remove DMSO. The aqueous layer was back extracted with EtOAc (3*) and the combined organic layer was dried (Na2SO4) and concentrated. The crude product was chromatographed through a Redi-Sep pre-packed silica gel column (120 g), eluding with a gradient of 0% to 30% EtOAc in hexane, to provide N-(4-(3-cyclopropylpyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine as tan solid. MS (ESI, pos. ion) m/z: 360.0 (M+1). IC50 (uM) +++++.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1227177-68-5, 3-Cyclopropyl-2-fluoropyridine.

Reference:
Patent; AMEN INC.; US2010/125062; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67346-74-1, 3-Ethynylpyridin-2-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Reference Example 67 3-(3-(4-Butoxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine; To a tetrahydrofuran (3 mL) solution of (4-butoxy-phenyl)-acetohydroximoyl chloride (150 mg, 0.619 mmol) described in Manufacturing Example 67-1-4 and 3-ethynyl-pyridin-2-ylamine (47 mg, 0.395 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (216 muL, 1.55 mmol) at room temperature, which was stirred for 2 hours at 50° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (27 mg, 14percent).1H-NMR Spectrum (CDCl3) delta (ppm): 0.95-0.99 (3H, m), 1.44-1.53 (2H, m), 1.72-1.79 (2H, m), 3.93-3.96 (2H, m), 4.00 (2H, s), 5.65 (2H, brs), 6.25 (1H, s),6.71-6.74 (1H, m), 6.86-6.88 (2H, m), 7.17-7.20 (2H, m), 7.72-7.75 (1H, m), 8.10-8.12(1H, m).

The synthetic route of 67346-74-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52313-50-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 52313-50-5, name is Picolinimidamide. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 2-(4-methyl-2-(naphthalen-2-yl)thiazol-5-yl)-5-(methylsulfonyl)-1,3,4-oxadiazole(9) (0.09 g, 0.25 mmol) in dry DMF (5 mL), the appropriateamine, hydrazine, guanidine or carboxamidine (0.4 mmol) was added.The reaction mixture was heated at 80 C for 0.5-12 h, and then pouredon ice water (50 mL). The formed solid was extracted with ethyl acetate(10 mL). The organic layer was evaporated under reduced pressure. Theobtained crude material was then purified by column chromatography.Physical properties and spectral analysis of isolated products are listed below:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52313-50-5, its application will become more common.

Reference:
Article; Hannoun, Mohamed H.; Hagras, Mohamed; Kotb, Ahmed; El-Attar, Abdul-Aziz M.M.; Abulkhair, Hamada S.; Bioorganic Chemistry; vol. 94; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 19337-97-4

Under N2 atmosphere, HOBt hydrate (0.31 g, ca. 2.0 mmol, MW = 125.12 + ca. 12 percent H20), EDCI (0.33 g ca. 2.1 mmol, MW = 155.25) and (£)-3-(3-pyridyl)acrylic acid (0.33 g, 2,2 mmol, MW = 149.137) were added sequentially to a cooled (0 °C) solution of 8 (0.515 g. 2 mmol, MW = 256.392) in dry CH2CI2 (7 mL). after stirring at 0 °C for 10 min N- methylmorpholine (0.44 mL) was added drop-wise under stirring at 0 °C. The mixture was then allowed to reach room temperature under stirring and stirred until completion of the reaction (monitored by TLC). A saturated aqueous solution of NaHC03 (15 mL) was added and stirred vigorously for 5 min. The aqueous layer was extracted with CH2CI2 (5 mL, 3 times). The combined organic extracts and solution were washed with brine (50 mL) and dried (MgS04). The solvent was evaporated in vacuo and the residue purified by FC (EtOAc) to give acrylamide 9 (0.643 g, 83 percent, MW = 387.513) as a yellow oil that was used directly in the following reaction. Solution of compound 9 (0.39 g, 1 mmol, MW = 387.513) in 4M HCI/dioxane solution (1 .0 mL) was stirred at 20 °C for 30 min (monitored by TLC). After solvent evaporation in vacuo, salt 9a (0.299 g, 92.3percent, MW = 323.889) was obtained as a white solid; it was used in the next step without purification. (0187) 1H NMR (400 MHz, CD3OD): delta = 9.15 (d, 1 H, J = 1 .5 Hz), 8.91 (dt, 1 H, J = 8.3 Hz, 1 .6 Hz), 8.86 (d, 1 H, J = 5.7 Hz), 8.17 (dd, 1 H, J = 8.2 Hz, 5.8 Hz), 7.67 (d, 1 H, J = 15.8 Hz), 7.06 (d, 1 H, J = 15.8 Hz), 3.62 (t, 2H, J = 6.1 Hz), 3.45 (t, 2H, J = 7.1 Hz), 3.35-3.31 (m, 3H), 3.19- 3.09 (m, 2H), 2.09-1 .99 (m, 2H), 1 .95-1 .84 (m, 4H). (0188) Yield: 0.53g (82percent), white solid, 1 H NMR (400 MHz, CD3OD): delta = 9.12 (d, 1 H, J = 1 .6 Hz), 8.90-8.83 (m, 2H), 8.15 (dd, 1 H, J = 8.2 Hz, 5.8 Hz), 7.67 (d, 1 H, J = 15.8 Hz), 7.01 (d, 1 H, J = 15.8 Hz), 3.42-3.34 (m, 4H), 2.99 (td, 2H, J = 12.7 Hz, 2.3 Hz), 2.02-1 .94 (m, 2H), 1 .69- 1 .58 (m, 3H), 1 .50-1 .34 (m, 6H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 19337-97-4, trans-3-(3-Pyridyl)acrylic acid.

Reference:
Patent; CENTRE HOSPITALIER UNIVERSITAIRE VAUDOIS CHUV; CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (CSIC); VOGEL, Pierre; DUCHOSAL, Michel; AIMABLE, Nahimana; INMACULADA, Robina; MOLLINEDO, Faustino; NENCIONI, Alessio; (105 pag.)WO2018/24907; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 885167-81-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 885167-81-7, name is 6-Bromo-5-methylnicotinaldehyde, molecular formula is C7H6BrNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Embodiment 69 (E)-2-((6-(3-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylstyryl)-5-methy lpyridin-3-yl)methylamino)-3-hydroxypropanoic acid 69 Synthetic route Synthesis of compound 69-a Compound 15-b (850mg, 2.2mmol) and 6-bromo-5-methyl nicotine aldehyde (300mg, 1.5mmol) were dissolved in a mixed solvent of 1,4-dioxane (20mL) and water (2mL), followed by addition of [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (30mg, 0.03mmol) and sodium carbonate (397mg, 3.7mmol). After the reaction system was purged three times with nitrogen, the reaction solution was heated to 80C and stirred for 12 hours. The reaction solution was cooled to room temperature and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to give compound 69-a as a yellow solid (220mg, yield 40%). LC-MS (ESI): m/z = 372 [M+H]+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 885167-81-7, 6-Bromo-5-methylnicotinaldehyde.

Reference:
Patent; Guangzhou Maxinovel Pharmaceuticals Co., Ltd.; WANG, Yuguang; XU, Zusheng; WU, Tianzhi; HE, Min; ZHANG, Nong; (113 pag.)EP3483142; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem