Pyridine-derivatives

Application of 1214334-70-9, 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. 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid. A new synthetic method of this compound is introduced below.

[0436] To a stirred solution of 5-bromo-6-methoxypicolinic acid (350 mg, 1 mmol) in CH2C12 (2 mL) under an argon atmosphere were added oxalyl chloride (347 mg, 2 mmol) and DMF (catalytic amount) at 0 C. The reaction mixture was stirred at room temperature for 2 h. After consumption of acid (by TLC), the volatiles were evaporated in vacuo to give 5- bromo-6-methoxypicolinoyl chloride.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214334-70-9, 5-Bromo-6-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 230301-11-8 , The common heterocyclic compound, 230301-11-8, name is tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, molecular formula is C11H17N3O2, 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.

A solution of 6-chloro-N-[4-ethyl-5-(4-fluorophenyl)-1H-pyrazol-3-yl]pyrimidin-4-amine (150 mg, 472 muetaiotaomicron) and tert-butyl 1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate (158 mg, 708 muiotaetaomicron, CAS 230301-11-8) in DMF (2.5 mL) was treated with caesium carbonate (461 mg, 1.42 mmol). The reaction mixture was stirred at 120C overnight and an additional night at 140C. The mixture was diluted with water, three times extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by preparative reverse phase HPLC (method: column: Reprosil CI 8; 10 muiotaeta; 125×30 mm / flow: 50 ml/min / eluent: A = water (0,01% formic acid), B = acetonitrile / gradient: 0.00-5.00 min = 10% B, 6.50 min = 20% B, 17.0-19.75 min = 100% B, 19.75-23.00 min = 90% B). Subsequently the obtained regioisomeric mixture was separated using (HPLC) method to yield 13.2 mg (6% yield) of the desired product. LC-MS (method 9): Rt = 1.18 min; MS (ESIpos): m/z = 505 [M+H]+1H-NMR (400 MHz, DMSO-d6) delta [ppm] : -0.008 (3.40), 0.008 (2.05), 0.988 (1.10), 1.007 (2.36), 1.025 (1.06), 1.073 (0.74), 1.091 (1.48), 1.108 (0.71), 1.424 (16.00), 2.328 (0.41), 2.519 (2.00), 2.524 (1.93), 3.214 (0.83), 3.375 (0.71), 3.392 (0.70), 3.593 (0.62), 3.607 (1.06), 3.621 (0.50), 4.382 (1.39), 7.339 (0.53), 7.361 (1.03), 7.383 (0.62), 7.586 (0.61), 7.600 (0.70), 7.622 (0.53), 7.661 (1.24), 8.459 (0.81), 9.416 (0.72), 12.813 (0.67).

The synthetic route of 230301-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; KLAR, Juergen; EHRMANN, Alexander; WILLWACHER, Jens; ENGEL, David; DIESKAU, Andre Philippe; KAHNERT, Antje; GROMOV, Alexey; SCHMECK, Carsten; LINDNER, Niels; MUeLLER, Thomas; ANDREEVSKI, Anna Lena; DREHER, Jan; COLLINS, Karl; (861 pag.)WO2018/69222; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54923-31-8, Adding some certain compound to certain chemical reactions, such as: 54923-31-8, name is 5-Bromo-6-methylpyridin-2-ol,molecular formula is C6H6BrNO, 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 54923-31-8.

The 0.60g in the reference embodiment of preparing 7 mentioned in 7A, the 0.38g 3-bromo-6-hydroxy-2-methylpyridine, 0.55g the potassium carbonate and 8 ml of a mixture of acetonitrile in the accompanying 80 C heating and stirring of 4 hours. The water added to the reaction mixture and the mixture is extracted with chloroform. The organic layer with saturated aqueous salt solution washing, drying by anhydrous magnesium sulfate, and concentrated under reduced pressure, to obtain 0.80g of 1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-methoxyphenyl]-4-methyl-1,4-dihydrotetrazole-5-one(called below 46A).

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. 54923-31-8, 5-Bromo-6-methylpyridin-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Co., Ltd.; Takayuki, Shiota; Masaki, Arimori; (241 pag.)CN105492432; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 571188-59-5, Adding some certain compound to certain chemical reactions, such as: 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate,molecular formula is C14H22N4O2, 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 571188-59-5.

To a solution of compound (11) (200.00 mg, 660.65 mumol, 1.00 eq) in dioxane (10.00 mL), compound (4) (220.67 mg, 792.79 mumol, 1.20 eq), Pd2(dba)3 (60.50 mg, 66.07 mumol, 0.10 eq) and Xantphos (76.45 mg, 132.13 mumol, 0.20 eq) and cesium carbonate (430.51 mg, 1.32 mmol, 2.00 eq) were added. The solution was heated to 110 C. under the protection of nitrogen gas and stirred for 16 hours. LCMS showed that the reaction was complete. The solution was cooled to 25 C., filtered and concentrated to obtain a crude product. The crude product was purified by preparative TLC (ethyl acetate:petroleum ether=1: 2) to obtain compound (12) (320.00 mg, 587.57 mumol, yield: 88.94%). LCMS (ESI) m/z: 545.3 (M+1).

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. 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Ding, Charles Z.; Chen, Shuhui; Hu, Lihong; Xu, Zhaobing; Liu, Yingchun; Ren, Bingjie; Li, Weidong; Li, Zongbin; Zhao, Rui; Zhang, Xiquan; (21 pag.)US2019/194168; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 7295-76-3, 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. 7295-76-3, name is 3-Methoxypyridine, molecular formula is C6H7NO, 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.

General procedure: To a stirred, cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2TMEDA[51] (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (1.0 mmol) at 0-10 C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solutionof Na2S2O3 (4 mL) and extraction with AcOEt (320 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by chromatographyon silica gel (the eluent is given in the product description) led to the compounds described below.

According to the analysis of related databases, 7295-76-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hedidi, Madani; Bentabed-Ababsa, Ghenia; Derdour, Aicha; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence; Tetrahedron; vol. 72; 17; (2016); p. 2196 – 2205;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 154048-89-2 , The common heterocyclic compound, 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine, 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.

Alternate Preparation: Tert-butyl 2-((benzyloxy)methyl)-lH-pyrrolo[2,3- c]pyridine-l-carboxylate was also prepared in an alternate preparation directly from tert-butyl tert-butyl (4-iodopyridin-3-yl)carbamate: In a sealed tube was added ((prop-2-yn-l-yloxy)methyl)benzene (104 mu, 0.750 mmol) and tert-butyl (4- iodopyridin-3-yl)carbamate (200 mg, 0.625 mmol) in DMF (625 mu). To this was added PdCl2(PPh3)2 (21.93 mg, 0.031 mmol), copper(I) iodide (11.90 mg, 0.062 mmol) and TEA (1742 mu, 12.50 mmol). This reaction was then degassed for 15 minutes and then allowed to stir at 80 C sealed. After 4 hours the reaction was complete. The reaction mixture was poured into ethyl acetate and saturated ammonium chloride. The organic was collected and washed several times with ammonium chloride. The organic was then purified on the biotage eluting in 10% ethyl acetate for 10 column volumes and then 10%-40% Ethyl acetate in hexanes over 10 column volumes. The product, tert-butyl 2-((benzyloxy)methyl)-lH- pyrrolo[2,3-c]pyridine-l-carboxylate (179 mg, 85% yield) was collected as a dark yellow oil. 1H NMR (400MHz, CHLOROFORM-d) delta = 9.58 – 9.20 (m, 1H), 8.70 – 8.42 (m, 1H), 7.54 – 7.34 (m, 6H), 6.78 (s, 1H), 4.98 (d, J=1.3 Hz, 2H), 4.73 (s, 2H), 1.69 (s, 9H).

The synthetic route of 154048-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MCDONALD, Ivar, M.; OLSON, Richard, E.; MATE, Robert, A.; WO2015/191401; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53234-55-2, 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. 53234-55-2, name is 5-Cyanopicolinic acid, molecular formula is C7H4N2O2, 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.

To a solution of 5-cyanopicolinic acid (1 g, 6.75 mmol) in dry THF (10 mL) at -15C was added Et3N (0.68 g, 6.75 mmol), ethyl chloro formate (0.73 g, 6.75 mmol),and the mixture was stirred for 16 hours at -15C. Ether (15 mL), TMSCHN2 (1.54 g, 13.5 mmol) was added, and the mixture was stirred overnight while returning to room temperature. After completion, the reaction mixture was diluted with EtOAc (75 mL), washed with water (50 mL), brine (40 mL), dried over anhydrous Na2SO4, filtered andevaporated. The diazaketone was dissolved in dioxane:H20 (1:1) (10 mL), added AgCOOPh (cat), and the mixture was stirred at 100C for 16 hours. After completion, the reaction mixture was diluted with EtOAc (50 mL), acidified using iN HC1 and extracted using EtOAc (2 x 50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude compound was purified by triturating with ether (10 mL) and pentane (50mL) to afford 2-(5-cyanopyridin-2-yl) acetic acid (350 mg, 32 %) as yellow 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 53234-55-2, 5-Cyanopicolinic acid.

Reference:
Patent; NUEVOLUTION A/S; SCHROeDER GLAD, Sanne; GROeN NOeRAGER, Niels; SARVARY, Ian; HAAHR GOULIAEV, Alex; TEUBER, Lene; STASI, Luigi, Piero; (244 pag.)WO2016/20288; (2016); 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. 886365-43-1, name is 5-Bromo-3-methylpicolinic acid. A new synthetic method of this compound is introduced below., Product Details of 886365-43-1

5-Cyano-3-methyl-pyridine-2-carboxylic acid The title compound was prepared by an analogous procedure to Acid-1 starting with 5-bromo-3-methyl-pyridine-2-carboxylic acid instead of the deuterated derivative [Acid-1 step a)]. Rf (hexanes/EtOAc 6:1)=0.28 1H-NMR (360 MHz, CDCl3): 8.09 (dd, 1H), 7.79 (ddd, 1H), 7.17 (t, 1H), 6.44 (t, J=45 Hz, 1H).

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, 886365-43-1, 5-Bromo-3-methylpicolinic acid.

Reference:
Patent; Novartis AG; US8338413; (2012); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 754131-60-7, 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. 754131-60-7, name is 3-Bromo-2-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

A solution of tert-butyl4-hydroxypiperidin-1-carboxylate (9.63 g) in THF (100 ml)was cooled to 0C, 60% sodium hydride (3.19 g) was added, and the mixture wasstirred for 20 min. To the reaction mixture was added a solution of3-bromo-2-(bromomethyl)pyridine (10.00 g) in THF (100 ml), and the mixture wasstirred at room temperature under an argon atmosphere overnight. To the mixture wasadded water at 0C, and the mixture was extracted with ethyl acetate. The organic layerwas washed with water and saturated brine, dried over anhydrous magnesium sulfate,and the solvent was evaporated under reduced pressure. The residue was purified bysilica gel chromatography (ethyl acetate/hexane) to give the title compound (13.12 g).MS, found: 371.1,373.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,754131-60-7, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FUJIMOTO Tatsuhiko; RIKIMARU Kentaro; FUKUDA Koichiro; SUGIMOTO Hiromichi; MATSUMOTO Takahiro; TOKUNAGA Norihito; HIROZANE Mariko; (166 pag.)WO2017/135306; (2017); 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. 17874-79-2, name is 5-(Methoxycarbonyl)picolinic acid, the common compound, a new synthetic route is introduced below. name: 5-(Methoxycarbonyl)picolinic acid

Reference Example 2 N-(2-t-Butoxycarbonylaminophenyl)-5-methoxycarbonylpyridine-2-carboxylic acid amide (Reference Compound No.2-1) HATU (21 g, 55 mmol) was added to a solution of 2-aminophenylcarbamic acid t-butyl ester (Reference Compound No.1-1, 10 g, 50 mmol), 5-methoxycarbonylpyridine-2-carboxylic acid (10 g, 55 mmol), and N-methylmorpholine (11 mL, 100 mmol) in DMF (100 mL), and then the reaction mixture was stirred at room temperature for 20 hours. Water (300 mL) was added thereto, and then the whole was extracted with ethyl acetate (300 mL) three times. The organic layer was washed with brine (200 mL), and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the obtained solid was collected by filtration to give 15 g of the title reference compound as a pale brown solid. (Yield 79%) 1H-NMR (400 MHz, CDCl3) delta 1.53 (s, 9H), 4.01 (s, 3H), 6.90 (br s, 1H), 7.20-7.25 (m, 2H), 7.51 (m, 1H), 7.82 (m, 1H), 8.38 (dd, J = 8.1, 0.7 Hz, 1H), 8.50 (dd, J = 8.1, 2.1 Hz, 1H), 9.18 (dd, J = 2.1, 0.7 Hz, 1H), 10.28 (br s, 1H)

The synthetic route of 17874-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Santen Pharmaceutical Co., Ltd; EP2133339; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem