Tag: M.W=300-400

Electric Literature of 74936-72-4, 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.74936-72-4, name is 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid, molecular formula is C16H16N2O6, molecular weight is 332.31, as common compound, the synthetic route is as follows.

(1) Preparation of (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid To a solution of 5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (700 g, 2.1 mol) in methanol (14 L) was added Quinidine (617 g, 1.90 mol). The mixture was stirred at 90 C. under reflux until Quinidine was completely dissolved. The stirring was continued for 3 hours. 4.5 L water was added. The stirring was continued for half an hour. The mixture was cooled down slowly. A solid was precipitated out and was filtered. The filter cake was treated with hydrochloric acid to produce (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (130 g) in a yield of 18.6%.

Statistics shows that 74936-72-4 is playing an increasingly important role. we look forward to future research findings about 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid.

Reference:
Patent; XUANZHU PHARMA CO., LTD.; Zhang, Hui; Fan, Mingwei; Sun, Liang; US2014/45896; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 473927-69-4, 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.473927-69-4, name is 1-(4-Iodophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one, molecular formula is C15H17IN2O2, molecular weight is 384.21, as common compound, the synthetic route is as follows.

Tetramethylethylenediamine (TMEDA, 27.2 mL) was dissolved in THF300 mL) in an inert atmosphere, then cooled to -78C before the drop-wise addition ofn-BuLi (67.6 mL, 2.5 M). 2-bromo-1,3-thiazole (15.2 mL) was added drop-wise and agitation was continued 30 minutes at -78C. Compound 1E (25 g, 139.50 mmol, 1.00 equiv) dissolved in THF (100 mL) was added drop-wise. Agitation was continued for 30 minutes at -78C then 2 hours at -10C. The reaction was neutralised with 500 mLof KHSO4 (sat.), then extracted 3 times with 1 litre of EtOAc. The organic phases were combined, washed twice with 400 mL water and twice with 700 mL of NaC1 (sat.), then dried over sodium sulfate, filtered and concentrated. The residue was purified on a silica column with a mixture of EtOAc and PE (1:100 to 1:10) to yield 25 g (88 %) of compound iF in the form of a yellow oil.

The chemical industry reduces the impact on the environment during synthesis 473927-69-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); 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. 1198416-32-8, name is 2-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., Computed Properties of C14H11BrN2O2S

A mixture of 209-3 (30 g, 0.085 mol), methanol (85OmL) and aqueous potassium hydroxide (5 mol/L, 100 mL) was heated under reflux overnight. The majority of the solvent was removed under vacuum, and the residue was partitioned between EtOAc and water. The organic layer was dried over anhydrous Na2SO4 and concentrated to give 209-4 (24 g, 80% yield) which was used without further purification. 1H NMR (400 MHz, DMSO): 6.550 (s, 1H); 7.039 (dd, J=5.2 Hz, J=3.2 Hz, 1H); 7.857 (dd, J=1.6 Hz, J=3.2 Hz, 1H); 8.155 (q, J=1.6 Hz, 1H); 12.418 (br, 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, 1198416-32-8, 2-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; INTERMUNE, INC.; US2009/318455; (2009); 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. 1357947-08-0, name is 5-Bromo-3-iodo-1H-pyrazolo[3,4-c]pyridine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo-3-iodo-1H-pyrazolo[3,4-c]pyridine

To a microwave tube was added 5-bromo-3-iodo-lH-pyrazolo[3,4-c]pyridine (100 mg, 0.31 mmol), pyridin-3-ylboronic acid (343 mg, 2.79 mmol), Pd(dppf)Cl2 (24 mg, 0.03 mmol), sodium carbonate (131 mg, 1.24 mmol), 1 ,2-dimethoxyethane (2 mL), ethanol (0.5 mL) and water (0.5 mL). The tube was flushed with nitrogen for 2 minutes and heated in a Biotage microwave at 160 C for 1 hour. The solvent was distilled off and the crude product was purified via reverse phase HPLC eluting with 15%> CH3CN in aqueous 10 mmol NH4HC03 to afford 176 as a pale yellow solid (30 mg, 28%). 1H NMR (500 MHz, DMSO) 1H NMR (500 MHz, DMSO) delta 14.1 (s, 1H), 9.44 (s, 1H), 9.37 (s, 3H), 9.26 (s, 1H), 8.71 (s, 1H), 8.67 – 8.66 (m, 1H), 8.60 – 8.59 (m, 2H), 8.56 -8.54 (m, 1H), 7.60 – 7.58 (m, 1H), 7.52 – 7.51 (m, 1H). ESI MS m/z = 274 (M+l)

The synthetic route of 1357947-08-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; LEE, Wendy; TSUI, Vickie Hsiao-Wei; WANG, Xiaojing; WEN, Zhaoyang; WO2013/24002; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1197294-80-6, 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 1197294-80-6, name is tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate (1.00 g, 2.66 mmol), 5-chloro-2-hydroxyphenylboronic acid (458 mg, 2.66 mmol) and sodium carbonate (1.13 g, 10.64 mmol) were combined and dissolved in a mixture of dioxane/water (14 mL/4 mL). The reaction mixture was degassed for 20 min with nitrogen and then tetrakistriphenylphosphinepalladium (0) (153 mg, 0.133 mmol) was added. The reaction mixture was heated at 70 C. for 18 hours and then partitioned between ethyl acetate (20 mL) and water (10 mL). The organic layer was separated, washed with brine (10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified on silica gel by Biotage (10% to 60% ethyl acetate in heptane over 20 CV) to give the title compound (700 mg, 66%) as a white solid.1H NMR (400 MHz, CD3OD): delta 1.40 (s, 9H), 3.50 (s, 8H), 6.80-6.90 (m, 2H), 6.95 (s, 1H), 7.15 (d, 1H), 7.30 (s, 1H), 8.05 (d, 1H).LCMS Rt=2.48 minutes MS m/z 388 [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 1197294-80-6, tert-Butyl 4-(4-bromopyridin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; ICAGEN INC.; PFIZER LIMITED; US2012/10182; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16727-47-2, 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.16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, molecular weight is 370.2398, as common compound, the synthetic route is as follows.

To the stirred solution of 2,6-bis(benzyloxy)-3-bromopyridine (16-1) (112.0 mg, 302 mumol) in Dioxane and water (7.5 mL) was added Pyridine-4-boronic acid 41-1 (42.1 mg, 453 mumol) and Potassium Phosphate (139 mg, 604 mumol). The reaction was degassed for 10 minutes and PdCl2(dppf)-DCM (24.6 mg, 30.2 mumol) was added. The reaction was refluxed at 90C for overnight. Reaction progress was monitored by TLC. Upon completion, the reaction was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and evaporated in vacuo. The product was purified by silica gel flash chromatography (4 g Isco gold, hexane/EtOAc 0-100%) to give 2,6-bis(benzyloxy)-3,4′-bipyridine (41-2) (90.0 mg, 244 mumol, 81.0 %) as a white solid. MS: ES+ 369.2

Statistics shows that 16727-47-2 is playing an increasingly important role. we look forward to future research findings about 2,6-Bis(benzyloxy)-3-bromopyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-52-4, 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. 884494-52-4, name is 3-Bromo-2-fluoro-4-iodopyridine. A new synthetic method of this compound is introduced below.

In a dry 3 neck 2 L flask equipped with a dry addition funnel, thermometer and stir bar was added 3- bromo-2-fluoro-4-iodopyridine (83.4 g, 276 mmol) followed by 300 mL of anhydrous THF under an atmosphere of nitrogen. The solution was cooled to -7O0C in 2-propanol/dry ice bath. A solution of isopropylmagnesium chloride 2.0 M in diethyl ether (145 mL, 290 mmol) was added drop wise over a period of 30 minutes. The solution was then stirred for 30 minutes before zinc (II) chloride 0.5 M in THF (276 mL, 138 mmol) was cannulated in. The solution was warmed to room temperature and stirred for lhour. The addition funnel was replaced with a reflux condenser and N4-cyclopentyl-5-iodopyrimidine-2,4-diamine (243, see example 200) (28.00 g, 92.1 mmol) was added, followed by Pd(PPh3)4 (5.32 g, 4.60 mmol). The solution was heated over night at a gentle reflux. After concentrating the solution to 1/1 Oth of the volume under vacuum, it was cooled in an ice bath. To this was added 100 mL of cold saturated NH4Cl, followed by 500 mL of water. 50OmL of 12% isopropanol/DCM was then added and the solution was stirred at room temperature for lhour before being filtered through filter paper. The filter cake was washed in succession with water, DCM and 12% 2-propanol /DCM. The filtrate was partitioned in a separation runnel and the aqueous layer was washed with 12% 2-propanol /DCM. The organics were dried over MgSO4 and then concentrated under vacuum. The residue obtained was partially dissolved in DCM with sonication and filtered off to give compound 244 (26.45g, 81.6%) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta ppm 8.18 (1 H, d, J= 4.9 Hz), 7.52 (1 H, s), 7.26 (1 H, dd, J= 4.9, 0.7 Hz), 6.34 (2 H, s), 6.12 (1 H, d, J= 7.6 Hz), 4.42 (1 H, sxt, J= 7.4 Hz), 1.76 – 1.96 (2 H, m), 1.55 – 1.68 (2 H, m), 1.31 – 1.53 (4 H, m) ) ppm; LCMS-ESI (POS), M/Z, M+l : Found 352.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-52-4, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55899-13-3, 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. 55899-13-3, name is 1-Amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate. A new synthetic method of this compound is introduced below.

Methyl 6-[(6-bromo-2-phenylpyrazolo[1,5-a]pyridin-3-yl)carbonyl]pyridine-2-carboxylate After potassium carbonate (6.25 g) was added to an N,N-dimethylformamide (22.6 mL) solution of methyl 6-(1-oxo-3-phenyl-2-propyn-1-yl)pyridine-2-carboxylate (3.00 g) and 1-amino-3-bromopyridinium 2,4,6-trimethylbenzenesulfonate (7.71 g) at room temperature, the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate, washed with water and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was evaporated and then the residue thus obtained was purified by silica gel column chromatography (n-hexane:ethyl acetate = 3:1) to obtain a title compound as a yellow crystal (1.35 g). 1H-NMR (400 MHz, CDCl3) delta 3.85 (3H, s), 7.05 (2H, t, J = 7.9 Hz), 7.13 (1H, t, J = 7.9 Hz), 7.23 (2H, d, J = 7.9 Hz), 7.59 (1H, dd, J = 9.1 and 1.8 Hz), 7.86 (1H, t, J = 7.9 Hz), 7.94 (1H, d, J = 7.9 Hz), 8.00 (1H, dd, J = 7.9 and 1.2 Hz), 8.28 (1H, d, J = 9.1 Hz), 8.73 (1H, d, J =1.8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55899-13-3, 1-Amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate, and friends who are interested can also refer to it.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; Kissei Pharmaceutical Co., Ltd.; SETO, Shigeki; UMEI, Kentaro; NISHIGAYA, Yosuke; TANIOKA, Asao; KONDO, Tatsuhiro; KONDO, Atsushi; TATANI, Kazuya; KAWAMURA, Naohiro; EP2669285; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1357947-08-0, 5-Bromo-3-iodo-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, Formula: C6H3BrIN3, blongs to pyridine-derivatives compound. Formula: C6H3BrIN3

The product from Step a (1.18 g, 3.65 mmol) was combined with doubly SEM-protected 1 ,3-dihydro-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-2//-bendimidazol-2- one (1.9 g, 3.65 mmol), and Pd(dppf)Ch (267 mg, 0.365 mmol) in dioxane (36.5 ml). A solution of 1 M aqueous Na2C03 (11.0 ml) was added, and the solution was sparged with nitrogen for one minute. The reaction was sealed and heated to 1 10 C for 15 hours, at which point the reaction was concentrated onto Celite and purified by flash chromatography over silica gel (ethyl acetate/hexanes 0% to 40%). Yield: 247 mg, (12%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1357947-08-0, 5-Bromo-3-iodo-1H-pyrazolo[3,4-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARCUS BIOSCIENCES, INC.; BEATTY, Joel; DEBIEN, Laurent Pierre Paul; DREW, Samuel Lawrie; FOURNIER, Jeremy; GRANGE, Rebecca Louise; JACOB, Steven Donald; JEFFREY, Jenna Leigh; LAWSON, Kenneth V.; LELETI, Manmohan Reddy; LINDSEY, Erick Allen; MANDAL, Debashis; POWERS, Jay Patrick; TRAN, Anh Thu; THOMAS-TRAN, Rhiannon; YAN, Xuelei; (164 pag.)WO2020/46813; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16727-47-2, 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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 2,6-bis(benzyloxy)-3-bromopyridine (16-1) (177 mg, 480 mumol), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 24-1 (100.0 mg, 480 mumol) and potassium phosphate (221 mg, 960 mumol) in water: dioxane (10 mL) was degassed with argon for 10 minute. PdCl2(dppf)-DCM (39.1 mg, 48.0 mumol) was added to above reaction mixture and the solution was again purged with argon and refluxed for 16 hour at 100C. After completion of the reaction was observed by TLC ( Rf = 0.5 in 30% EtOH/Hexane), the reaction mixture was filtered through celite and concentrated. The residue was again dissolved in EtOAc (50 mL), washed with water, brine and evaporated. The crude residue was purified by combi flash chromatography (4 g Isco gold, hexane/EtOAc 70-30%) to give 2,6-bis(benzyloxy)-3-(1-methyl- 1H-pyrazol-3-yl)pyridine 24-2 (120 mg, 323 mumol, 67.4 %) as a white gummy solid. 1H NMR (400 MHz, DMSO-d6) delta 8.17 (d, J = 8.2 Hz, 1H), 7.65 (d, J = 1.9 Hz, 1H), 7.46-7.42 (m, 4H), 7.39-7.33 (m, 4H), 7.33-7.31 (m, 2H), 6.61 (d, J = 2.1 Hz, 1H), 6.51-6.49 (m, 1H), 5.46 (s, 2H), 5.37 (s, 2H), 3.85 (s, 3H). Synthesis

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16727-47-2, 2,6-Bis(benzyloxy)-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem