Tag: M.W=300-400

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.96428-50-1, name is Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, molecular formula is C18H18N2O3, molecular weight is 310.35, as common compound, the synthetic route is as follows.Product Details of 96428-50-1

Example 2A 8-(Benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid 253 ml of 2N aqueous sodium hydroxide solution were added to a solution of 15.7 g (50.59 mmol) of ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate in 253 ml of dioxane, and the mixture was stirred at room temperature for 14 hours. 101 ml of 6N hydrochloric acid were then added to the mixture. The solid formed was filtered off, washed with water and with methyl tert-butyl ether and then dried in a vacuum drying cabinet at 40 C. overnight. This gave 15.49 g (108% of theory) of 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid as a colourless solid. The yield was more than 100% owing to water of crystallization (1H NMR). LC-MS (Method 1): Rt=0.66 min MS (ESpos): m/z=283.0 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=2.67 (s, 3H), 3.2-3.8 (very broad water peak), 5.41 (s, 2H), 7.30 (m, 1H), 7.35-7.48 (m, 4H), 7.57 (d, 2H), 9.02 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96428-50-1, Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
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. 944937-30-8, name is Methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, molecular formula is C9H7IN2O2, 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. HPLC of Formula: C9H7IN2O2

Step 2. 1-tert-butyl 5-methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-1,5-dicarboxylate To a mixture of methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (700 mg, 2.32 mmol) in dichloromethane (10 mL) and tetrahydrofuran (10 mL) was added N,N-diisopropylethylamine (1.21 mL, 6.95 mmol), di-tert-butyldicarbonate (607 mg, 2.78 mmol), and 4-dimethylaminopyridine (28 mg, 23 mmol). The reaction was allowed to stir at room temperature for 16 hours. The reaction was concentrated and purification by flash column chromatography (0-50% ethyl acetate/heptanes) gave the title compound (760 mg, 82%) as a solid. +APCI (M+H) 403.3; 1H NMR (400 MHz, DMSO-d6, delta): 8.93 (d, J=2.0 Hz, 1H), 8.16 (d, J=2.0 Hz, 1H), 8.14 (s, 1H), 3.91 (s, 3H), 1.59 (s, 9H).

With the rapid development of chemical substances, we look forward to future research findings about 944937-30-8.

Reference:
Patent; PFIZER INC.; US2012/270893; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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

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.96428-50-1, name is Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, molecular formula is C18H18N2O3, molecular weight is 310.35, as common compound, the synthetic route is as follows.Product Details of 96428-50-1

Example 2A 8-(Benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid 253 ml of 2N aqueous sodium hydroxide solution were added to a solution of 15.7 g (50.59 mmol) of ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate in 253 ml of dioxane, and the mixture was stirred at room temperature for 14 hours. 101 ml of 6N hydrochloric acid were then added to the mixture. The solid formed was filtered off, washed with water and with methyl tert-butyl ether and then dried in a vacuum drying cabinet at 40 C. overnight. This gave 15.49 g (108% of theory) of 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid as a colourless solid. The yield was more than 100% owing to water of crystallization (1H NMR). LC-MS (Method 1): Rt=0.66 min MS (ESpos): m/z=283.0 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=2.67 (s, 3H), 3.2-3.8 (very broad water peak), 5.41 (s, 2H), 7.30 (m, 1H), 7.35-7.48 (m, 4H), 7.57 (d, 2H), 9.02 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96428-50-1, Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
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. 944937-30-8, name is Methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, molecular formula is C9H7IN2O2, 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. HPLC of Formula: C9H7IN2O2

Step 2. 1-tert-butyl 5-methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-1,5-dicarboxylate To a mixture of methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (700 mg, 2.32 mmol) in dichloromethane (10 mL) and tetrahydrofuran (10 mL) was added N,N-diisopropylethylamine (1.21 mL, 6.95 mmol), di-tert-butyldicarbonate (607 mg, 2.78 mmol), and 4-dimethylaminopyridine (28 mg, 23 mmol). The reaction was allowed to stir at room temperature for 16 hours. The reaction was concentrated and purification by flash column chromatography (0-50% ethyl acetate/heptanes) gave the title compound (760 mg, 82%) as a solid. +APCI (M+H) 403.3; 1H NMR (400 MHz, DMSO-d6, delta): 8.93 (d, J=2.0 Hz, 1H), 8.16 (d, J=2.0 Hz, 1H), 8.14 (s, 1H), 3.91 (s, 3H), 1.59 (s, 9H).

With the rapid development of chemical substances, we look forward to future research findings about 944937-30-8.

Reference:
Patent; PFIZER INC.; US2012/270893; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem