Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 929617-35-6, 5-Bromo-1H-pyrazolo[3,4-c]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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A suspension of 5-bromo-lH-pyrazolo[3,4-c]pyridine (760 mg, 3.80 mmol) in DCM (10 mL) was treated with DMAP (50 mg, 0.41 mmol) and Boc20 (1.00 g, 4.58 mmol). After stirring for 20 min, a homogeneous solution had formed. The reaction was stirred another 12 hours, after which it was washed with 1 N aqueous HCl, water, dried (Na2S04) and concentrated to dryness, providing tert-butyl 5-bromo-lH-pyrazolo[3,4-c]pyridine-l- carboxylate: MS (EI) calc’d for CiiHi3BrN302 [M+H]+ 298 and 300, found 298 and 300; 1H MR (600 MHz, CDC13) delta 9.30 (s, 1 H), 8.16 (s, 1 H), 7.83 (s, 1 H), 1.71 (s, 9 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,929617-35-6, 5-Bromo-1H-pyrazolo[3,4-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SILIPHAIVANH, Phieng; METHOT, Joey; LIPFORD, Kathryn Ann; MOLINARI, Danielle; SLOMAN, David, L.; WITTER, David; ZHOU, Hua; BOYCE, Christopher; HUANG, Xianhai; LIM, Jongwon; GUERIN, David; KARUNAKARAN, Ganesh Babu; BAKSHI, Raman Kumar; LIU, Ziping; FU, Jianmin; WAN, Zhilong; LIU, Wei; (216 pag.)WO2016/100050; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 38940-62-4, 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.38940-62-4, name is 3-Acetyl-5-bromopyridine, molecular formula is C7H6BrNO, molecular weight is 200.03, as common compound, the synthetic route is as follows.

Commercially available 3-acetyl-5- bromopyridine (6.53 g, 32.8 mmol), solid NaOH (13.1 g, 326 mmol), and hydrazine hydrate (13 mL) was heated in di ethylene glycol (25 mL) at 140 0C for 4 hours. The reaction mixture was partitioned between ether and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give an oil. This was dissolved in tetrahydrofuran (40 mL) and cooled to 0 0C. Isopropylmagnesiumchloride (20 mL, 2.0 M in THF) was syringed in and the reaction mixture was stirred for 2 hours at room temperature. N,N-dimethylformamide (7 mL) in tetrahydrofuran (15 mL) was added and stirring was continued for. an additional hour. The solution was quenched with 2 N HCl to pH of 3 then partitioned between ethyl acetate and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography to give 3- ethyl-5-formylpyridine (0.78 g, 18%) as a solid. 1H NMR (DMSO-^6): delta 10.1 (s, IH), 8.91 (s, IH), 8.71 (s, IH), 8.00 (s, IH), 2.75 (q, 2H), 1.31 (t, 3H). MS m/z calculated for (M + H)+ 152, found 152.

The chemical industry reduces the impact on the environment during synthesis 38940-62-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
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. 106984-91-2, name is 6-Oxo-1,6-dihydropyridine-3-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 106984-91-2

To a stirred solution of 5-3 (O.lg, 0.3mMol) and triethylamine (0.08mL, 0.5mMol) in NMR (ImL) was added 17-2 (0.03g, 0.3mMol) and acetic acid (0.03mL, 0.5mMol), followed by sodium triacetoxyborohydride (0.12g, 0.5mMol). After stirring overnight at room temperature, the reaction was filtered through a syringe filter and purified on a Cl 8 reverse phase HPLC to yield 17-3 as the HCl salt. Mass (M+l) calculated: 473.2085 observed: 473.2092.

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, 106984-91-2, 6-Oxo-1,6-dihydropyridine-3-carbaldehyde.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 154048-89-2 ,Some common heterocyclic compound, 154048-89-2, molecular formula is C10H13IN2O2, 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.

tert-Butyl [2,4′-bipyridin]-3′-ylcarbamate. To a pressure vessel was added tert- butyl (4-iodopyridin-3-yl)carbamate (0.25g, 0.781 mmol), 2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)pyridine (0.176 g, 0.859 mmol) and PdC12(dppf)- CH2C12Adduct (0.032 g, 0.039 mmol). The reaction mixture was degassed and flushed with N2 (3x). Then Dioxane (5) was added and the system was degassed and flushed with N2(3x). SODIUM CARBONATE (0.781 ml, 1.562 mmol) was added and the system was degassed and flushed with N2(3x). The reaction mixture was heated to 85 C for 3h. The reaction was diluted with ethyl acetate and satd ammonium chloride. The org layer was washed with water, brine and dried over sodium sulfate. The crude product was dissolved in a small amount of dichloromethane and charged to 1 lOg silica gel cartridge which was eluted with 0- 100% ethyl acetate / hexanes over a period of 60 mins. The desired fractions were combined and dried under vacuo to give tert-butyl [2,4′-bipyridin]-3′-ylcarbamate (0.02 g, 0.074 mmol, 9.44 % yield). MS (ESI) (m/z): 272.1(M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,154048-89-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; VRUDHULA, Vivekananda M.; PAN, Senliang; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69594; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 874959-68-9, 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. 874959-68-9, name is 5-Bromopyridine-2-sulfonyl chloride. A new synthetic method of this compound is introduced below.

Ethyl 5-amino-3-methylbenzofuran-2-carboxylate (0.23 g, 1.05 mmol), 5-bromopyridine-2-sulfonyl chloride (0.54 g, 2.10 mmol), potassium carbonate(0.29 g, 2.10 mmol) was added successively to 30 mL of dichloromethane, and the mixture was stirred overnight at room temperature, and potassium carbonate was filtered off, and the residue was purified by column chromatography to yield 0.43 g (yield: 93.3%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,874959-68-9, 5-Bromopyridine-2-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; You Qidong; Wei Jinlian; Jiang Zhengyu; Guo Xiaoke; Xu Xiaoli; Zhang Xiaojin; (44 pag.)CN107619384; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19337-97-4, 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 19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Compound 1-3 (1.3 g, 3 mmol) was dissolved in dichloromethane (10 ml)Trifluoroacetic acid (2 ml) was added,The reaction was carried out at room temperature for 2 hours, and the solvent was distilled off under reduced pressure to give a brown oil. The oil was dissolved in dichloromethane (20 ml)N, N-diisopropylethylamine (1.6 ml, 9 mmol) was added successively,Trans-3 (3-pyridyl) allyl acid(448 mg, 3 mmol),EDCI (1.7 g, 9 mmol),DMAP (73 mg, 0.6 mmol), reacted at room temperature for 4 hours,Saturated ammonium chloride (20 ml) was added and extracted with dichloromethane (20 ml x 3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure and subjected to column chromatography to give Compound 1 ((E) -N- 3- (2-amino-6- (cyclopropylamino) pyrimidin-4-yl) phenyl) -5- (3- (pyridin-3-yl) acrylamido) pentanamide) (0.9 g, %).

According to the analysis of related databases, 19337-97-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Guangzhou Bio-pharmaceutical And Health Institute; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; China Pharmaceutical University; Jiang Sheng; Tu Zhengchao; Zhu Jidong; Yao Hequan; Yao Yiwu; Tan Xiaochu; Gu Shoulai; Qiu Yatao; (30 pag.)CN106928192; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 113118-81-3 ,Some common heterocyclic compound, 113118-81-3, molecular formula is C6H4BrNO, 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 solution of methyltriphenylphosphine bromide (3.16 g, 8.87 mmol) in tetrahydrofuran (20 ml.) is added sodium hexamethyldisilazane (1 M solution in THF, 9.67 ml_, 9.67 mmol) dropwise. The reaction mixture is stirred at room temperature for 30 min, whereupon 5-bromo-pyridine-3-carbaldehyde (1.5 g, 8.06 mmol) is added. The reaction mixture is allowed to stir at room temperature for 1 h. The mixture is concentrated and the residue is purified by silica gel flash chromatography (heptane- ethyl acetate, 7:3) to afford 3-bromo-5-vinyl-pyridine as a colorless oil. MS (ESI) m/z 185.91 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-81-3, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2009/156462; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1480-87-1 ,Some common heterocyclic compound, 1480-87-1, molecular formula is C5H3FN2O2, 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 flask charged with toluene (37.3 mL) were added trans-N-boc- 1 ,4- cyclohexanediamine (2.00 g, 9.33 mmol), potassium carbonate (1.290 g, 9.33 mmol) and 2-fluoro-3-nitropyridine (commercially available from Matrix Scientific, Columbia, SC) (1.326 mL, 9.33 mmol). The resulting bright yellow solution was heated overnight at 120C leading to conversion to the desired product as the primary species along with a more polar impurity according to LC-MS. The mixture was diluted with water, transferred to a separatory funnel and extracted with EtOAc (2x). The combined organic layers were dried with Na2S04, filtered, and dried under reduced pressure providing a bright yellow solid which was triturated with DCM providing tert-butyl ((lr,4r)-4-((3-nitropyridin-2-yl)amino)cyclohexyl)carbamate (1.51 g, 4.49 mmol, 48.1 % yield) as a bright yellow solid. lH NMR (400 MHz, DMSO-d6) delta = 8.49 (dd, J = 1.8, 4.5 Hz, 1 H), 8.41 (dd, J= 1.8, 8.4 Hz, 1 H), 8.06 (d, J= 7.7 Hz, 1 H), 6.79 – 6.69 (m, 2 H), 4.13 – 4.00 (m, J= 3.9, 7.4, 7.4, 1 1.3 Hz, 1 H), 3.29 – 3.20 (m, 1 H), 2.01 – 1.92 (m, 2 H), 1.82 (d, J= 10.6 Hz, 2 H), 1.55 – 1.41 (m, 2 H), 1.38 (s, 9 H), 1.35 – 1.21 (m, 2 H). m/z (ESI) 281.2 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1480-87-1, its application will become more common.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Hongbing; HUANG, Xin; MARTIN, Matthew, W.; PATEL, Vinod; WO2013/134079; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55304-75-1, 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 55304-75-1, name is 2,6-Dichloro-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of compound 2e1 (64 mg, 0.30 mmol), morpholine (0.027 mL, 0.31 mmol) and triethylamine (0.050 mL, 0.36 mmol) in DMF (1 mL) is stirred overnight at ambient temperature. The mixture is then diluted with EtOAc and successively washed with water (4×) and brine. The organic phase is dried with MgSO4, filtered and concentrated to afford intermediate 2e2.

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 55304-75-1, 2,6-Dichloro-3-(trifluoromethyl)pyridine.

Reference:
Patent; Beaulieu, Pierre L.; Coulombe, Rene; Fazal, Gulrez; Goulet, Sylvie; Poirier, Martin; Rancourt, Jean; Stammers, Timothy; Thavonekham, Bounkham; US2008/45516; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 849020-87-7, Adding some certain compound to certain chemical reactions, such as: 849020-87-7, name is 6-Hydroxy-4-(trifluoromethyl)nicotinic acid,molecular formula is C7H4F3NO3, 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 849020-87-7.

In a 10 niL microwave vial to a suspension of 6-hydroxy-4-(trifluoromethyl)nicotinic acid (1048 mg, 5.06 mmol) in pyridine, anhydrous (6139 mu, 76 mmol) was added slowly diethyl chlorophosphate (749 mu, 5.19 mmol) at RT in an atmosphere of nitrogen. The reaction mixture was stirred at rt for 2 h. The suspension turned into a solution and then into a suspension again. To this, 5-bromo- 4-fluoro-2-((3S,5R)-3,4,5-trimethylpiperazin-1-yl)aniline (400 mg, 1.265 mmol) was added and the reaction was heated at 70 C for 3 h. After completion, pyridine was removed in vacuo and the residue partitioned between dichloromethane (3 mL) and saturated sodium bicarbonate solution (3 mL). The suspension was stirred for 10 min. The organic layer was separated, and dried over anhydrous Na2SC>4. The solvent was evaporated in vacuo yielding the crude product which was purified by flash column chromatography on silica gel (0-100%, 89% CH2C12, 10% MeOH, 1% NH4Ac/CH2Cl2) to afford the title compound (192 mg, 30%). 11H NMR (500 MHz, MeOD) delta 8.10 (d, J = 7.4 Hz, 1H), 7.92 (s, 1H), 7.09 (d, J = 10.1 Hz, 1H), 6.90 (s, 1H), 3.00 (d, J = 11.0 Hz, 2H), 2.57 (t, J = 11.0 Hz, 2H), 2.54 – 2.49 (m, 2H), 2.35 (s, 3H), 1.14 (d, J= 6.0 Hz, 6H); LCMS [M+l]+ = 505.00.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 849020-87-7, 6-Hydroxy-4-(trifluoromethyl)nicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem