Day: March 15, 2022

Synthetic Route of 902837-42-7, 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 902837-42-7, name is 7-Bromo-1H-pyrrolo[3,2-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 7-bromo-1H-pyrrolo[3,2-C]pyridine (700 mg, 3.55 mmol) in DMF (7 mL) was added sodium hydride (171 mg, 4.26 mmol). The resulting mixture was stirred for 0.5 hours at 25 C. Methyl iodide (656 mg, 4.62 mmol) was added and stirred for 1 hour. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (30 mL*2). The combined ethyl acetate layers were washed with water and brine, dried over Na2SO4, and concentrated in vacuo to give 7-bromo-1-methyl-pyrrolo[3,2-c]pyridine (640 mg, 81% yield) as a yellow solid. LCMS (ESI): [M+H]+=211.0.

According to the analysis of related databases, 902837-42-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); 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. 3222-56-8, name is 2-Methylnicotinic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C7H7NO2

I chloride (1.90 mL, 21.8 mmol) was added to 2-methyl nicotinic acid (1.50 g, 10.9 mmol) in anhydrous dichloromethane (20 mL) with triethylamine (1.6 mL, 11.5 mmol) and the reaction mixture was kept at room temperature overnight before the solvent was removed. THF was added to the residue and ammonia gas was bubbled through for 2 h. The THF was removed and the residue was dissolved into methanol and water and the pH was adjusted to 10.0 with potassium carbonate. The mixture was concentrated. After column chromatography the desired amide was isolated (1.10 g, 73.8%). [0439] NaH (0.428 g, 10.7 mmol, 60% in mineral oil) was added to 4-hydroxy-3,5-dimethylbenzonitrile (1.50 g, 10 mmol) in anhydrous DMF (8 mL). Benzyl bromide (1.83 g, 10.7 mmol) was added and the reaction was kept at room temperature overnight. The reaction mixture was poured into water. The isolated solid was further washed with hexane to yield the desired ether building block (2.0 g, 84.3%). It was used in the next reaction without further purification. The above amide (0.65 g, 4.77 mmol) in anhydrous THF (15 mL) was added drop-wise to BuLi (7.5 mL, 1.60 M) at -20 C. The reaction mixture was kept at this temperature for 1 h and then the above ether building block (1.13 g, 4.77 mmol) in THF (20 mL) was added drop-wise at -20 C. and the reaction was stirred for 1.5 h. The reaction temperature was increased to room temperature and continued for a further 1 h. Water (20 mL) was added and the mixture was stirred for a while before the solvent was removed and the residue was purified by column chromatography to yield the desired intermediate (0.50 g, 29.4%). A 50 mL flask was charged with the above described intermediate (0.50 g, 0.0014 mol) and pyridine hydrogen chloride (2.4 g, 0.014 mol) and the mixture was heated to 180 C. for 1.5 h. The mixture was cooled and poured into methanol (4 mL), then filtered. The collected solid was further washed with ethyl acetate and dried to give 7-(4-hydroxy-3,5-dimethylphenyl)-1,6-naphthyridin-5(6H)-one (350 mg, 82.7%) as an HCl salt. Selected data: MS (ES) m/z: 266; MP >350 C.

The synthetic route of 3222-56-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter Ronald; US2013/281397; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58553-48-3, 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.58553-48-3, name is 5-(Hydroxymethyl)picolinonitrile, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

5-(Hydroxymethyl)pyridine-2-carbonitrile (4 g, 0.03 mol; see step (ii) above) was dissolved in 25 mL of methylene chloride and cooled in an ice bath. Mesyl chloride (2.32 mL, 0.0300 mol) and then triethylamine (4.6 mL, 0.033 mol) were added dropwise. The reaction mixture was stirred and after work up the crude mesylate was treated with NaN3 (7.35 g, 0. 113mol) in 20 mL of DMF. The reaction mixture was stirred at 40 C. for 2 h, diluted with water and extracted with ethyl acetate. The organic layer was concentrated to yield 3.95 g (83%) of the crude azide.

Statistics shows that 58553-48-3 is playing an increasingly important role. we look forward to future research findings about 5-(Hydroxymethyl)picolinonitrile.

Reference:
Patent; Inghardt, Tord; Johansson, Anders; Svensson, Arne; US2004/19033; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 64951-08-2, 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. 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below.

ER-879054-00: As depicted in Scheme 47 above, ER-824188-00 (20.0 mg, 0.0538 mmol) was dissolved in NMP (0.500 mL). Added Imidazo[l,2-a]pyridine-2- carboxylic acid (49.9 mg, 0.308 mmol). Added N,N,N’,N’-Tetramethyl-O-(7- azabenzotriazol-l-yl)uranium hexafluorophosphate (51.2 mg, 0.134 mmol) in NMP (0.500 mL). The reaction was heated at 1000C for 5 minutes in the microwave. The reaction was not complete so it was stirred at room temperature overnight. The mixture was filtered. Purification by LC/MS followed by evaporation using the genevac provided ER-879054-00 (8.6 mg, 31%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; SPYVEE, Mark; CHEN, Qian; CARLSON, Eric; KUSANO, Kuzutomi; WO2011/11494; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, 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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

To a vial were added 2,6-dibromo-4-methylpyridine (121 mg, 0.482 mmol), cw-butyl 4- [l-hydroxy-l-(l,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate (75 mg, 0.241 mmol), potassium carbonate (100 mg, 0.722 mmol), pivalic acid (5.59 mu, 0.048 mmol),tetrakis(triphenylphosphine)palladium(0) (11.1 mg, 9.63 mu?iotaomicronGamma) and N,N-dimethylacetamide (760 mu). The vial was sealed and placed under argon through 3 cycles of evacuation and argon flushing then reacted at 80 C overnight. The resulting mixture was cooled, diluted with ethyl acetate, filtered through a plug of CELITE and concentrated. The residue was purified by column chromatography on silica gel (0-100% ethyl acetate/hexanes) to afford racemic-cw-butyl 4- { 1 -[5-(6-bromo-4-methylpyridin-2-yl)- 1 ,3 -thiazol-2-yl]- 1 -hydroxyethyl } – cyclohexanecarboxylate.Two enantiomers were separated by chiral super critical fluid chromatography (ChiralTechnology IC-H, 2.1 x 25 cm, 5 uM, 70/30 ethanol/C02, Flow Rate: 70 mL/min, 8 min run time, WL: 220 nm). Elution was observed at 5.20 min and 6.08 min. Pooled fractions of each peak were concentrated under reduced pressure.Enantiomer 1 (retention time 5.20 min): MS ESI calc’d. for C22H29BrF3N203S [M + H+] 481 and 483, found 481 and 483.Enantiomer 2 (retention time 6.08 min): MS ESI calc’d. for C22H29BrF3N203S [M + H+] 481 and 483, found 481 and 483.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73112-16-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; DI FRANCESCO, Maria Emilia; HAIDLE, Andrew, M.; OTTE, Ryan, D.; ELLIS, John Michael; CHILDERS, Kaleen Konrad; NORTHRUP, Alan, B.; YANG, Liping; WO2012/154520; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13958-86-6, 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. 13958-86-6, name is 5-Methylpyridine-3,4-diamine, molecular formula is C6H9N3, 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.

The cyclization with 2,3-difluorbenzoic acid in PPA was performed as described above. Purified by column chromatography (silica gel, eluent: dichloromethan/methanol = 12/1). Yield: 22.2%.

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 13958-86-6, 5-Methylpyridine-3,4-diamine.

Reference:
Patent; K.U. LEUVEN RESEARCH & DEVELOPMENT; GILEAD SCIENCES, INC.; PUERSTINGER, Gerhard; WO2005/63744; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, 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, COA of Formula: C12H8ClNO, blongs to pyridine-derivatives compound. COA of Formula: C12H8ClNO

4-chlorophenylpyridyl ketone (43.5mg, 0.2mmol), dibromantin (57.2mg, 0.2mmol) and Pd (OAc) 2 (4.5mg, 0.02mmol), 2mL of dichloroethane, 90C The reaction was carried out for 12 hours and purified by thin layer chromatography to obtain 30.2 mg of 2-bromo-4-chlorophenylpyridylmethanone, with a yield of 50.9%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, and friends who are interested can also refer to it.

Reference:
Patent; China Three Gorges University; Liu Qixing; Chen Yongsheng; Zhang Yin; Chen Danyi; Wen Simiaomiao; Zhao Rongrong; Liu Yiheng; Zhou Haifeng; (14 pag.)CN110563641; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72093-03-9, 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.72093-03-9, name is 3-Chloro-2-methylpyridine, molecular formula is C6H6ClN, molecular weight is 127.57, as common compound, the synthetic route is as follows.

To a solution of 3-chloro-2-methylpyridine (0.367 g, 2.88 mmol) in THF (10 mL) was added 0.65 M (2,2,6,6-tetramethylpiperidin-1-yl)zinc(II) lithium chloride (6.65 ml, 4.32 mmol) at ft. The resulting yellow solution was stirred at sametemperature for 1 h, scandium trifluoromethanesulfonate (0.057 g, 0.115 mmol) was added and stirred at room temperature for 15 mm. A microwave vial was charge with 3 -(8-(bis(4-methoxybenzyl)amino)-2-bromo- [1 ,2,4jtriazolo[ 1 ,5-ajpyrazin-6- yl)benzonitrile (0.64 g, 1.152 mmol), palladium acetate (0.021 g, 0.092 mmol) and 2?-(dicyclohexylphosphino)-N,N,N?,N?-tetramethylbiphenyl-2,6-diamine (0.080g, 0.184 mmol) was evacuated under high vacuum and backfilled with nitrogen. The mixture was cooled to 0 C and the zinc reagent was added slowly via syringe. Afier addition, the reaction was heated to 60 C for lh. The reaction solutionwas partitioned between EtOAc and sat. NH4C1 solution. The layers were separated and the aqueous extracted further with EtOAc (2x). The combined organicswere washed with water and brine, dried over MgSO4, and concentrated. The resulting residue was purified via flash chromatography to afford the product. LC-MS calculated for C34H29C1N702 (M+H): mlz = 602.2; found 602.2.

The chemical industry reduces the impact on the environment during synthesis 72093-03-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INCYTE CORPORATION; HOANG, Gia; WANG, Xiaozhao; CARLSEN, Peter Niels; GAN, Pei; LI, Yong; QI, Chao; WU, Liangxing; YAO, Wenqing; YU, Zhiyong; ZHU, Wenyu; (333 pag.)WO2020/10197; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886371-28-4, 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. 886371-28-4, name is 3-Bromo-6-chloroimidazo[1,2-a]pyridine, molecular formula is C7H4BrClN2, 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 an oven dried 5 mL microwave vessel was addedPd(dppf)Cl2·CH2Cl2 (4 mol%), halide/pseudohalide (1 equiv),boron coupling partner (1 equiv), and Cs2CO3 (3 equiv). Thevessel was then capped and purged with N2 before addition ofCyrene (1 mL, 0.25 M) and H2O (1.8 mL). The reaction mixturewas heated to 50 C and maintained at this temperature withstirring for 5 h before the vessel was vented and decapped. Thesolution was then diluted with Et2O (10 mL) and washed withwater (2 × 20 mL) and brine (2 × 20 mL). The organics were thenpassed through a hydrophobic frit and concentrated underreduced pressure to give a residue, which was purified by flashchromatography (silica gel) to afford the title compound.

According to the analysis of related databases, 886371-28-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wilson, Kirsty L.; Murray, Jane; Jamieson, Craig; Watson, Allan J. B.; Synlett; vol. 29; 5; (2018); p. 650 – 654;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-43-6, 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 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 3-hydroxy-2,6-dimethylpyridine (20 mg, 0.17 mmol) in DMF (1.4 mL) is added NaH (95%, 5 mg, 0.21 mmol). The mixture is stirred for about 15 minutes before benzylchloride 3a4 (75 mg, 0.14 mmol) is added. The mixture is stirred at RT overnight. Methanol (0.5 mL) and LiOH (60 mg, 1.4 mmol) are added and the mixture is further stirred at RT overnight. The mixture is acidified with AcOH and purified by preparative HPLC to isolate compound 1058.

According to the analysis of related databases, 1122-43-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/18656; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem