Category: pyridine-derivatives

Related Products of 870997-85-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.870997-85-6, name is 3-Amino-5-bromopyridine-2-carboxylic Acid, molecular formula is C6H5BrN2O2, molecular weight is 217.0201, as common compound, the synthetic route is as follows.

Step 1: 3-Amino-5-(4-trifluoromethoxy-phenylsulfanyl)-pyridine-2-carboxylic acid: [00273] A solution of 3-amino-5-bromo-pyridine-2-carboxylic acid (Int 1, 3.26 g, 15 mmol), 4- trifluoromethoxy-benzenethiol (CAS: 169685-29-4, 3.5 g, 18 mmol) and DBU (2.22 mL, 15 mmol) was prepared in DMA (15 mL). This mixture was heated at 140 C for 45 minutes in a microwave reactor. Next, the mixture was diluted with a mixture of 1% AcOH in water. A suspension was obtained that was subsequently filtered. This collected solid was washed with a 101 ABV12212USO1 1% AcOH/water mixture followed by washing with petroleum ether. After drying in a vacuum oven, the titled compound was obtained

The chemical industry reduces the impact on the environment during synthesis 870997-85-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; ALTENBACH, Robert, J.; COWART, Marlon, D.; DE MUNCK, Tom, Roger Lisette; DROPSIT MONTOVERT, Sebastien Jean, Jacques Cedric; GFESSER, Gregory, A.; KELGTERMANS, Hans; MARTINA, Sebastien, Laurent Xavier; VAN DER PLAS, Steven, Emiel; WANG, Xueqing; (300 pag.)WO2016/193812; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 38496-18-3, 2,6-Dichloronicotinic acid, 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, name: 2,6-Dichloronicotinic acid, blongs to pyridine-derivatives compound. name: 2,6-Dichloronicotinic acid

Preparation Example A-4. 2-Amino-6-chloronicotinic acid Tris(2-(2-methoxyethoxy)ethyl)amine (3.0mL, 9.4mmol) was added to a mixture of 2,6-dichloronicotinic acid (40g (90percentpurity), 0.19 mol), acetamide (80g, 1.4mol), potassium carbonate (78g, 0.56mol), copper(I) chloride (0.93g, 9.4mmol) and xylene (80mL), which was stirred overnight at 145°C. After cooling, copper(I) chloride (0.46g, 4.6mmol) was added to the reaction solution, which was stirred overnight at 145°C. After cooling the reaction solution to 105°C, water (1 00mL) was added, the solution was stirred for 1 hour at the same temperature, and cooled down to room temperature. 5N hydrochloric acid (150mL) was added, the solution was neutralized with a citric acid aqueous solution, then, ethyl acetate was added, and the solution was filtered through Celite pad. The organic layer was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate), recrystallization by the ethyl acetate-hexane was carried out to obtain the title compound (1.4g, 8.3mmol, 4.5percent) as white crystal. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 6.61 (1H, d, J=8.1 Hz), 7.53 (2H, brs), 8.01 (1 H, d, J=8.1 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38496-18-3, 2,6-Dichloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1121-76-2, 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 1121-76-2, name is 4-Chloropyridine 1-oxide. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of (4-chloropheny)methanol (49.5 g, 347 mmol) inTHF (200 mL) was added dropwise to a suspension of NaH (60%oil dispersion, 16.7 g, 419 mmol) in THF (200 mL) at 0 C. Afterthe mixture was stirred at 0 C for 30 min, 4 (45.0 g, 347 mmol)was added portionwise to the reaction mixture. After completionof the addition, the mixture was stirred at rt for 5 h. The mixturewas quenched with water (400 mL) at 0 C and extracted withEtOAc/THF (1:1) four times. The organic layers were combined,passed through NH-silica gel pad (EtOAc/MeOH) and concentrated.The filtrate was concentrated, and the residual solid was washedwith IPE and dried to give the title compound (54.3 g, 66%) as abrown solid.

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 1121-76-2, 4-Chloropyridine 1-oxide.

Reference:
Article; Igawa, Hideyuki; Takahashi, Masashi; Ikoma, Minoru; Kaku, Hiromi; Kakegawa, Keiko; Kina, Asato; Aida, Jumpei; Okuda, Shoki; Kawata, Yayoi; Noguchi, Toshihiro; Hotta, Natsu; Yamamoto, Syunsuke; Nakayama, Masaharu; Nagisa, Yasutaka; Kasai, Shizuo; Maekawa, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 24; 11; (2016); p. 2504 – 2518;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 88511-27-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.88511-27-7, name is 4-Amino-3-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.

General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.2 mg, 0.05 mmol), 4-amino-3-iodopyridine(1) (220 mg, 1.00 mmol), tert-butylamine (0.315 mL, 3.00 mmol)(or the given amount of primary or secondary amine (Table 1)) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) under argon in a 100 mL autoclave. The atmosphere was changed to carbonmonoxide and pressurized to 40 bar. The reaction was conducted for the given reaction time upon stirring at 50C and analysed by TLC. The autoclave was vented, the reaction mixture was concen-trated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (320 mL). The organic phase was dried over Na2SO4, filtered and evaporated to a solid material. All compounds were subjected to column chromatography ((Silicagel 60 (Merck), 0.063 e 0.200 mm); MeOH/CHCl3 orMeOH/EtOAc/CHCl3 (the exact ratios are specied in Characterization (4.4.) for each compound)).

Statistics shows that 88511-27-7 is playing an increasingly important role. we look forward to future research findings about 4-Amino-3-iodopyridine.

Reference:
Article; Szoke, Gyoengyi; Takacs, Attila; Berente, Zoltan; Petz, Andrea; Kollar, Laszlo; Tetrahedron; vol. 72; 22; (2016); p. 3063 – 3067;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 152126-31-3, name is 3-Fluoropicolinic acid, molecular formula is C6H4FNO2, 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. Computed Properties of C6H4FNO2

General method for Examples 43-48Carboxylic acid (0.266 mmol), DMF (0.5 ml.) and DIPEA (0.084 ml.) were added to a Greenhouse Plus tube. HATU (101 mg) in DMF (1 ml.) was added and the reaction was stirred for 1 h. Methyl 5-(4-aminophenyl)-3-[[(frans-4-methylcyclohexyl)carbonyl](1- methylethyl)amino]-2-thiophenecarboxylate (100 mg, a synthesis of which is described as Intermediate 9) in DMF (1 ml.) was then added and the reaction was stirred at room temperature for 24 h. The solvent was evaporated in vacuo using a Genevac vacuum centrifuge. To the residue was added THF (1 ml_), MeOH (1 ml.) and 2M lithium hydroxide solution (1 ml_). The reaction was stirred for 24 h and was then neutralised with 2N HCI (1 ml_). The mixture was partitioned between EtOAc and water and the organic phases were separated and dried using a hydrophobic frit. The organic phases were evaporated in vacuo using a Genevac vacuum centrifuge and the crude material was purified by MDAP HPLC to give the title compound-Example 435-(4-{[(3-Fluoro-2-pyridinyl)carbonyl]amino}phenyl)-3-[[(frans-4- methylcyclohexyl)carbonyl](1 -methylethyl)amino]-2-thiophenecarboxylic acidMS calcd for (C28H30FN3O4S + H)+: 524MS found (electrospray): (M+H)+ = 5241H NMR (de-DMSO): delta 10.81 (1 H, s), 8.59 (1 H, s), 8.00-7.68 (6H, m), 7.43 (1 H, s), 4.73 (1 H, quintet), 2.01 (1 H, t), 1.70-1.39 (5H, m), 1.31-1.10 (5H, m), 0.90 (3H, d), 0.73 (3H, d), 0.71-0.48 (2H, m), 1 exchangeable proton not seen.

With the rapid development of chemical substances, we look forward to future research findings about 152126-31-3.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/59042; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.Application In Synthesis of 3-Amino-2-chloro-6-(trifluoromethyl)pyridine

A solution of 3-amino-2-chloro-6-trifluoromethyl-pyridine (0.890 g), 4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-l-carboxylic acid tert-butyl ester (1.4 g) (prepared as described in WO 2006/003494) and tetrakis(triphenyl- phosphine)palladium (0.200 g) in 1 ,2-dimethoxyethane (45 ml) was treated with aqueous potassium phosphate (1.1 M) (1.92 g). The reaction mixture was stirred at 800C for 3 hours. Aqueous workup with ethyl acetate furnished a residue which was purified by chromatography on silica gel (eluent: hexane / ethyl acetate 1 :1) to give 3-amino-6- trifluoromethyl-3′,6′-dihydro-2’H-[2,4′]bipyridinyl-r-carboxylic acid tert-butyl ester (1.5 g) as a white solid. MS (ES+) 288 (M-isoprene); IH NMR (400 MHz, CDCl3) 1.50 (s, 9H), 2.61 (m, 2H), 3.67 (t, 2H), 4.10 (m, 2H), 4.21 (s, 2H), 6.11 (s, IH), 7.03 (d, IH), 7.33 (d, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; PITTERNA, Thomas; CASSAYRE, Jerome Yves; CORSI, Camilla; MAIENFISCH, Peter; WO2010/9968; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 137178-88-2 ,Some common heterocyclic compound, 137178-88-2, molecular formula is C6H3BrClNO, 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.

To a stirred solution/suspension of 5-bromo-2-pyridinecarboxylic acid (0.2 g, 1 mmol) in CH2Cl2 (25 mL) was added oxalyl chloride (0.26 mL, 3 mmol) and 1 drop of DMF. Gas evolved and the all the solids dissolved. After Ih the reaction was evaporated and pumped. This material was dissolved/suspended in CH3CN (10 mL) then Intermediate C (0.25 g, 1 mmol) and diisopropylethylamine (2 mL) were added. A white solid formed(DIEA.HCl). After 1.5 h the reaction was filtered and the filtrate was evaporated, taken up in CH2Cl2, filtered and chromatographed on silica gel, eluting with a gradient of 0-10% methanol +1% ammonium hydroxide in CH2CI2. The product fractions were evaporated, dissolved in CBD2CI2, washed with 1 M NaOH (to remove residual hydrochloride salt) and evaporated to afford 0.25g of 24A (58% yield). 1H NMR (300 MHz, DMSOd5) 69.30 (t, /= 6.4 Hz, IH), 8.78 (d, J= 2.1 Hz, IH), 8.25(dd, J= 2.3 Hz, J= 8.2 Hz, IH), 7.98 (d, J= 8.3 Hz, IH), 7.19 (t, J= 7.8 Hz, IH), 6.88 – 6.80 (m, 2H), 6.74 – 6.68 (m, IH), 4.50 (t, J= 4.9 Hz, IH), 4.43 (d, J= 6.4 Hz, 2H), 3.03 – 2.96 (m, 2H), 2.52 – 2.47 (m, 3H), 2.03 – 1.87 (m, 6H), 1.77 – 1.68 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,137178-88-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2007/78251; (2007); 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. 159870-80-1, name is 5-Fluoro-2-iodopyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C5H3FIN

General procedure: Pyridines substituted at the 2-position with halides shown in Tables 2 and 3 are stirred in a mixture of toluene (900 mL) and anhydrous ether (600 mL). The resulting solutions were cooled to < -100 C for 20 min at which point n-BuLi/hexane was added slowly over 22 min. After maintaining the temperature below -100 C for 20 min, triisopropylborate was added dropwise, and then the reaction mixture was stirred below -70 C. After stirring for 4 h, ether (500 mL) was added and the solution was allowed to stand overnight at room temp. Isopropanol was added (30mL), then the reaction mixture was stirred for 30 min, the allowed to stand without stirring for an additional 2 h. The resulting precipitate was collected by filtration then washed with ethyl ether and dried under nitrogen atmosphere for 1.5 h. The resulting triisopropoxy analog was treated with a mixture of acetone and water (450 mL/50 mL) to remove any contaminating n-butylborate lithium salt. The solids were collected by filtration, washed with acetone/water (9:1, 300 mL), and dried in air for 2h, then lyophilized overnight to afford product. The synthetic route of 159870-80-1 has been constantly updated, and we look forward to future research findings. Reference:
Article; Chen, Kuanchiang; Peterson, Richard; Math, Shivanand K.; Lamunyon, James B.; Testa, Charles A.; Cefalo, Dustin R.; Tetrahedron Letters; vol. 53; 36; (2012); p. 4873 – 4876;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 174669-74-0 ,Some common heterocyclic compound, 174669-74-0, molecular formula is C5H4FNO, 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.

2-Fluoro-3-methoxypyridine (3): 2-Fluoropyridin-3-ol (10 mmol),methyl iodide (20 mmol) and potassium carbonate (20 mmol) in acetone (100 ml) was refluxed overnight. The inorganic salt wasfiltered and the solvent was evaporated. The residue was purified oncolumn (eluent: EtOAc:hexane = 1:5) to afford a colorless liquid [19](95%). 1H NMR (CDCl3): d 7.74-7.75 (m, 1H, C6-H), 7.26-7.31 (m, 1H,C4-H), 7.11-7.15 (m, 1H, C5-H), 3.91 (s, 3H, OMe). 19F NMR (CDCl3): d90.15 (s). ESI-MS: 128 (M+1)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,174669-74-0, its application will become more common.

Reference:
Article; Ma, Yongmin; Hider, Robert C.; Journal of Fluorine Chemistry; vol. 173; (2015); p. 29 – 34;,
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. 107512-34-5, name is 4-Chloro-3-methoxy-2-methylpyridine. A new synthetic method of this compound is introduced below., COA of Formula: C7H8ClNO

Step 1, the 12 parts by weight of the acidic phosphotungstic acid dissolved in water prepared for mass concentration 25% phosphotungstic acid solution;Step 2, weighing 220 parts by weight of 4 – chloro -3 – methoxy -2 – methyl pyridine, slowly added under stirring step 1 bedded phosphotungstic acid solution, stirring to complete mixing, heating in water bath temperature is raised to 87 C, dropwise 350 parts by weight of the mass concentration is 35% hydrogen peroxide, hydrogen peroxide is accelerated-rate drop 60 parts by weight/hours; then in 85 C lower heat insulating 5 hours, to obtain the reaction solution;Step 3, the reaction cooling to 30 C is added after a dilute alkali solution (mass concentration 12% sodium hydroxide aqueous solution) adjusted to pH 7 – 9, then the dichloromethane extraction, water washing extract in neutral, adds anhydrously Na2SO4Drying, at a temperature of 35 – 45 C, pressure 0.06 – 0.08 mpa evaporating the dichloromethane under reduced pressure, to obtain 230.2 parts by weight of the obtained 4 – chloro -3 – methoxy -2 – methyl pyridine – N – oxide; high performance liquid chromatogram of the product, the product appearance time is as shown in Figure 7, 3.740 min, according to the appearance time can be qualitative verification product; product 4 – chloro -3 – methoxy -2 – methyl pyridine – N – oxide of high purity, according to the area of the yield of the product is calculated unitary method 95%.

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, 107512-34-5, 4-Chloro-3-methoxy-2-methylpyridine.

Reference:
Patent; Anhui Jin He Industrial Co., Ltd.; Chuzhou College; Xia Jiaxin; Wang Yonggui; Ge Xiutao; Geng Qingbao; Yang Zhijian; (10 pag.)CN107129466; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem