Tag: M.W:100-200

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 184416-84-0, name is 2,3-Dichloroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 184416-84-0

2,3-Dichloro-isonicotinic acid methyl ester[00197] To a suspension of 2,3-dichloro-isonicotinic acid (7.7 g, 40 mmol) in dichloromethane (45 mL) were added DMF (0.1 mL) and oxalyl chloride (17.5 mL, 200 mmol). The reaction mixture was stirred at room temperature for 18 hours and then concentrated under reduced pressure. The resultant residue was azeotroped with toluene, then cooled to 00C and dissolved in methanol (135 mL). The mixture was allowed to warm to room temperature and then concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate and the resulting solution was washed with a saturated solution of sodium hydrogen carbonate, water and brine, dried (Na2SO4), filtered and concentrated to give the title compound as a colourless oil that crystallised on standing (7.9 g, 96%). 1H NMR (CDCl3, 400MHz) 8.38 (d, J = 5.0 Hz, IH), 7.52 (d, J = 5.0 Hz, IH), 3.99 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 184416-84-0.

Reference:
Patent; GENENTECH, INC.; WO2009/85980; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 22918-01-0, 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.22918-01-0, name is 2-Bromo-4-chloropyridine, molecular formula is C5H3BrClN, molecular weight is 192.441, as common compound, the synthetic route is as follows.

Preparation of 2-bromo-3-methyl-4-chloro-pyridine To a solution of 2,2,6,6-tetramethyl-pyridine (21.1 mL, 125 mmol) in freshly distilled THF (120 mL) at -78C was added nBuLi (50 mL, 125 mmol) in 30 min. The resulting mixture was stirred at -78C for 30 min and was added through a cannula over 30 min to a solution of 3-bromo-4-chloro-pyridine (20.0 g, 104 mmol) in freshly distilled THF (60 mL) that had been cooled to -78C prior to the addition. The reaction mixture was stirred at -78C for 30 min before iodomethane (7.78 mL, 125 mmol) was added over a period of 10 min. The reaction was stirred at -78C for 30 min and was allowed to warm up to room temperature prior to be quenched with aqueous NH4Cl (65 mL). The aqueous phase was extracted with ethyl acetate (2X150 mL). The organic phases were separated, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 5:1) to afford the title compound as a yellow solid (10.6 g, 49%). 1H NMR (CDCl3, 300 MHz) delta ppm: 8.10 (d, J = 5.1 Hz, 1 H), 7.27 (d, J = 5.1 Hz, 1H), 2.51 (s, 3 H).

The chemical industry reduces the impact on the environment during synthesis 22918-01-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Emergent Product Development Gaithersburg Inc.; Roussel, Patrick; Heim, Jutta; Schneider, Peter; Bartels, Christian; Liu, Yaoquan; Dale, Glenn; Milligan, Daniel; (107 pag.)EP3034078; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 107867-51-6, 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 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: A mixture of compound 1.2 (0.2 mmol) and thiocarbonyldiimidazole (0.2 mmol) in dry THF (2.0 mL) was stirred at room temperature for 30 minutes under an atmosphere of N2. 5-Trifluoromethyl-pyridine-2,3-diamine (0.2 mmol) was added and the reaction stirred at room temperature until the reaction was deemed complete. The reaction mixture was then treated with N,N’-dicyclohexylcarbodiimide (0.2 mmol) and the resulting mixture was stirred at 40-60 C. for several hours. The solvent was removed and the residue was purified by preparative HPLC to give the titled compound. 1H NMR (CD3OD, 400 MHz): delta 8.76 (s, 1H), 8.51 (s, 1H), 8.38 (s, 1H), 7.95 (s, 1H), 7.56 (d, J=7.3 Hz, 2H), 7.48 (s, 1H), 7.38 (d, J=6.4 Hz, 2H), 4.03 (s, 2H), 3.09 (s, 2H) ppm; EIMS (m/z): 456.1 (M++H).

According to the analysis of related databases, 107867-51-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lew, Willard; Baskaran, Subramanian; Oslob, Johan D.; Yoburn, Joshua C.; Zhong, Min; US2006/35908; (2006); 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. 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., name: Imidazo[1,2-a]pyridine-2-carboxylic acid

Step (a) tert-butyl {cis-4-[(imidazo[l,2-a]pyridin-2- ylcarbonyl)amino] cyclohexyl} carbamate, O Imidazo[l,2a]pyridine-2-carboxyli acid (5 g, 30.8 mmol) was dissolved in NMP (200 ml) and DIEA (11.96 g, 16.43 ml) was added, followed by O-(7-Azabezotriazol-l-yl)- N,N,N’,N’-tetramethyluronium hexafluorophosphate (14.07 g, 37 mmol). The reaction was stirred for 5 min. (4-Amino-cyclohexyl)-carbamic acid tert-butyl ester (6.61 g, 30.8 mmol) was then added and the solution stirred at room temperature ovenight. Water was added and the product extracted with ethyl acetate. The organic phase was dried (anhydrous magnesium sulphate), filtered and concentrated in vacuo to afford the sub-title compound (8.5 g, contains some NMP). This was used without further purification. APCI (+ve) m/z: 359 [M+H]

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, 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84223; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52687-85-1, Imidazo[1,2-a]pyridin-2(3H)-one hydrochloride, 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, Recommanded Product: Imidazo[1,2-a]pyridin-2(3H)-one hydrochloride, blongs to pyridine-derivatives compound. Recommanded Product: Imidazo[1,2-a]pyridin-2(3H)-one hydrochloride

EXAMPLE 1 STR11 A mixture of 341 g (2 mols) of imidazo[1,2-a]pyridin-2(3H)-one hydrochloride and 700 ml of water is treated with portions of a solution of 80 g (2 mols) of sodium hydroxide in 200 ml of water, with stirring. A solution of 250.7 g (2.16 mols) of maleic acid in 600 ml of water is then added dropwise in such a way that the internal temperature of the reaction mixture remains between 40 C. and 45 C. After 30 hours at room temperature (20-25 C.), the mixture is cooled to 5 C., the precipitate formed is filtered off, the filtrate is concentrated to about half its volume in vacuo, and the product which has precipitated is filtered off with suction. The combined residues are washed with a small amount of cold methanol and dried at 50 C. in vacuo. This gives 400 g of 3-(1,2-dicarboxyethyl)-imidazo[1,2-a]pyridin-2(3H)-one with a melting point of 193 (decomposition).

The synthetic route of 52687-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4480106; (1984); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54401-85-3 ,Some common heterocyclic compound, 54401-85-3, molecular formula is C9H11NO2, 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. 4-Pyridineethanol Fifteen grams (0.091 mol) of 4-pyridineacetic acid ethyl ester was dissolved in 180 ml of dry THF. The solution was transferred to a 1 l., 3-neck round bottom flask which had been flushed with nitrogen. To the mixture was added dropwise 55 ml of 1.0 M lithium aluminum hydride (0.055 mol) at approximately 0 C. The reaction mixture became yellow upon addition of the reducing agent. Following addition, the mixture was quenched with 2.1 ml of water at 0 C. followed by 2.1 ml of 15% by volume of sodium hydroxide and 6.3 ml of water. The mixture was allowed to stir at room temperature for approximately 4 hours and filtered through Celite. The filtrate was concentrated under vacuum to provide 6.38 g of 4-pyridineethanol. This material was used directly in the following reaction.

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. 54401-85-3, Ethyl 4-pyridylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; US4968678; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 688782-02-7, 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. 688782-02-7, name is 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

To a mixture of 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine (0.20 g, 1.20 mmol), Pd(OAc)2 (0.013 g, 0.060 mmol) and Xantphos (0.069 g, 0.12 mmol) in dioxane (3.0 mL, 1.200 mmol) under Ar gas was added methyl 3-mercaptopropanoate (0.15 mL, 1.32 mmol) and Hunig’s base (0.42 mL, 2.4 mmol). The reaction was heated to 150C under argon in a microwave reactor for 2 hours. 3-mercaptopropanoate (0.15 mL, 1.32 mmol) was added and heated to 200C in the microwave reactor for 2 hours. The reaction mixture was cooled and diluted with EtOAc (25 mL) and filtered through celite. The filtrate was concentrated and the resulting residue was purified by flash chromatography with a 0 to 10% MeOH in EtOAc gradient. The material was subjected to a DCM trituration to afford methyl 3-((3-methyl-1H- pyrrolo[2,3-b]pyridin-4-yl)thio)propanoate (0.042 g, 0.17 mmol, 14 % yield). m/z (esi/APCI) M+1 = 251.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,688782-02-7, 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; BLAKE, James F.; BOYS, Mark Laurence; CHICARELLI, Mark Joseph; COOK, Adam; ELSAYED, Mohamed S. A.; FELL, Jay B.; FISCHER, John P.; HINKLIN, Ronald Jay; MCNULTY, Oren T.; MEJIA, Macedonio J.; RODRIGUEZ, Martha E.; WONG, Christina E.; (259 pag.)WO2020/81848; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 42373-30-8, 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. 42373-30-8, name is 4-Aminonicotinaldehyde, molecular formula is C6H6N2O, 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.

Step 4: A solution of 4-aminonicotinaldehyde (57 mg, 0.47 mmol) in tetrahydrofuran was cooled in an ice bath and lithium aluminium hydride (27 mg, 0.70 mmol, 1.5 eq) was added. The ice bath was removed and the reaction mixture was sittred for 30 min. TLC showed complete consumption of starting material. The reaction mixture was quenched with water (1 mL) and 1 N HCl (2 mL) was added extracted with ethylacetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was used for the next reaction with in a crude state (60 mg, 99%).

According to the analysis of related databases, 42373-30-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; Christoph, Thomas; Lesch, Bernhard; Lee, Jeewoo; US2013/29961; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71670-70-7, 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 71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

3-fluoro-4-nitrophenol (200.0 g, 1.27 mol) was added to a solution of 2-(chloromethyl)-5-methylpyridine hydrochloride (222 g, 1.25 mol), powdered potassium carbonate (383.6 g, 2.75 mol), potassium iodide (207 g, 1.25 mol), and acetonitrile (3.4 L). The resulting mixture was stirred at 60 Celsius for 2 h. The reaction was cooled to RT, concentrated to dryness and partitioned between H2O (1.5 L) and ethyl acetate (1.5 L). The organic layers were separated and the aqueous layer was extracted with ethyl acetate (1.0 L). The combined organic layers were washed with brine (1 L) then dried over magnesium sulfate, filtered, and concentrated to dryness. The crude solid was recrystallized from i-PrOH (1.5 L) at 70 Celsius. After cooling to 0 Celsius the solid was collected by filtration and rinsed with i-PrOH (2×200 mL) and heptanes (2×200 mL) to yield the title compound as a dark solid (242.0 g, 73.9%). MS (ESI): mass calcd. for C13H11FN2O3, 262.10; m/z found, 263.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 8.44 (s, 1H), 8.16 (t, J=9.2, 1H), 7.76-7.62 (m, 1H), 7.45 (d, J=7.9, 1H), 7.30 (dd, J=13.7, 2.5, 1H), 7.07 (dd, J=9.3, 1.9, 1H), 5.30 (s, 2H), 2.31 (s, 3H).

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 71670-70-7, 2-(Chloromethyl)-5-methylpyridine hydrochloride.

Reference:
Patent; Chai, Wenying; Dvorak, Curt A.; Eccles, Wendy; Edwards, James P.; Goldberg, Steven D.; Krawczuk, Paul J.; Lebsack, Alec D.; Liu, Jing; Pippel, Daniel J.; Sales, Zachary S.; Tanis, Virginia M.; Tichenor, Mark S.; Wiener, John J. M.; US2014/275029; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1003711-43-0, 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 1003711-43-0, name is 2-Bromo-5-hydroxy-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-oxazolemethanol (1.12 g, 11.30 mmol, Combi-Blocks Inc.) and triphenylphosphine (3.72 g, 14.18 mmol) in THF (20 mL) was added 2-bromo-5- hydroxy-3-picoline (2.27 g, 12.07 mmol, AOB Chem USA). The mixture was cooled to 0 C and 1 ,2-ethoxycarbonyl diazene (2.5 mL, 13.72 mmol) was added slowly. The solution was slowly allowed to warm to RT. After 21 h, diisopropyl azodicarboxylate (1.5 mL, 7.63 mmol) was added to the mixture. About 1.5 h later, a second batch of diisopropyl azodicarboxylate (1.5 mL, 7.63 mmol) was added. The mixture was stirred at RT for an additional 4 h and was diluted with EtOAc (50 mL). The solution was washed with NaOH (0.5 N, 10 mL), water, brine, and then dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (10-50% EtOAc in DCM) to afford 2-(((6-bromo-5-methylpyrid in-3-yl)oxy)methyl)oxazole (3.8 g, ~80% pure) as a white solid that contained the hydrazine by-product as impurities (based on 1H-NMR). LCMS (ESI, pos.) 269.0 (M+1 )+. 1H NMR (400 MHz, CHLOROFORM-d) delta 8.02 (d, J=2.93 Hz, 1 H), 7.70 (d, J=0.78 Hz, 1 H), 7.23 (d, J=2.74 Hz, 1 H), 7.17 (s, 1 H), 5.18 (s, 2H), 2.37 (s, 3H).

According to the analysis of related databases, 1003711-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem