Tag: M.W:200-300

Application of 588729-99-1, 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. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, molecular formula is C5H4BrClN2, 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.

c) N-(5 -bromo-2-chloro-3 -pyridinyl)benzenesulfonamide. To a stirred solution of 3-amino-5-bromo-2-chloropyridine (24 mmol) in dichloromethane (50 mL) was added pyridine (37 mmol) followed by benzenesulfonyl chloride (35 mmol) drop wise over 5 min. The reaction mixture was stirred at room temperature for 18 h and evaporated to dryness in vacuo. The residue was purified by flash chromatography on silica gel (15% hexanes/dichloromethane then 0-5% ethyl acetate in 15% hexanes/dichloromethane). During evaporation of the solvents the product precipitated. The resultant slurry was diluted with hexanes, filtered, and dried under vacuum to give the title compound (2.89 g, 34%) as a white solid. MS (ES) m/e 346.7 (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 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/39140; (2009); 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. 52833-94-0, name is 2-Amino-5-bromonicotinic acid. A new synthetic method of this compound is introduced below., Recommanded Product: 2-Amino-5-bromonicotinic acid

To a mixture of 2-amino-5-bromonicotinic acid (1 g, 4.61 mmol) and (1-(1-(tert- butoxycarbonyl)piperidin-4-yl)-1H-pyrazol-4-yl)boronic acid pinacol ester (2.6 g, 6.91 mmol) in 25 mL of 1,4-dioxane/ water (3/1) was added K2CO3 (1.9 g, 13.8 mmol) followed by Pd(PPh3)4 (0.26 g, 0.23 mmol). The reaction mixture was heated at 100 C for 3 h, cooled to room temperature, and partitioned between water and ethyl acetate. Water layer was separated and adjusted to pH value around 5. The precipitate was collected by filtration and triturated in mixture of methanol and water. The precipitate was filtered. The wet cake was dried to afford 1.5 g of the title compound. The crude product was used for the next step without further purification. MS (ESI, m/z): 388.1 [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, 52833-94-0, 2-Amino-5-bromonicotinic acid.

Reference:
Patent; DONG-A SOCIO HOLDINGS CO., LTD.; KIM, Hadong; RYU, Ki Moon; PARK, Seong Jin; YOON, Taeyoung; JANG, Mi Yeon; KIM, Jin Kwan; (419 pag.)WO2018/71343; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73290-22-9, Adding some certain compound to certain chemical reactions, such as: 73290-22-9, name is 2-Bromo-5-iodopyridine,molecular formula is C5H3BrIN, 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 73290-22-9.

To the solution of (2-methoxyphenyl)boronic acid (0.471 g, 3.1 mmol) in 1 ,4-dioxane(20 mL), 2-bromo-5-iodopyridine (1.lg, 3.87 mmol), potassium phosphate tribasic(2.46 g, 11 .61 mmol) and water (5 mL) was added. The reaction mixture wasdegasified for 10 mm under nitrogen before the addition of Pd(PPh3)4 (0.224 g, 0.194mmol) to it. The reaction mixture was then heated at 70C for 1 h. The reactionmixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous Na2SO4. The organic layer was concentrated under vacuo to yield crude product, which was purified by column chromatography to yield title compound (0.72 g, 87.09%) as a colourless liquid.LCMS: (M+H) = 264-266; 1H NMR: (ODd3, 300MHz) 68.43-8.44 (d, 1H), 7.65-7.68 (dd, 1H), 7.42-7.45 (d, 1H), 7.29-7.34 (t, 1H), 7.19-7.23 (m, 1H), 6.99-7.01 (d, 1H), 6.92-6.96 (m, 1 H), 3.75 (5, 3H).

According to the analysis of related databases, 73290-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 120277-69-2, 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. 120277-69-2, name is 3-Bromo-5-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below.

To a suspension of sodium hydride (60% in mineral oil, 0.044 g, 1.09 mmol) in DMF (2 mL) was added pyrrolidin-2-one (0.081 g, 0.945 mmol) and the reaction mixture was stirred at room temperature for 20 min. Then, 3-bromo-5-chloromethyl-pyridine (0.15 g, 0.727 mmol) was added and the resulting suspension was heated at 60 C. over night. The mixture was quenched with water (2 mL) and extracted with EtOAc (2×10 mL). Combined organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.217 g, 87%) as a white solid. MS: 251.1, 257.1 (M+H+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,120277-69-2, 3-Bromo-5-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Aebi, Johannes; Amrein, Kurt; Hornsperger, Benoit; Knust, Henner; Kuhn, Bernd; Liu, Yongfu; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; Zhou, Mingwei; US2013/72679; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 19755-53-4, name is 2-Bromo-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Bromo-3-nitropyridine

Example 16; 1-(2-(benzo[b]thiophen-2-yl)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea; 16a. 2-(benzo[b]thiophen-2-yl)-3-nitropyridine; To a solution of 2-bromo-3-nitropyridine (75 mg, 0.371 mmol) in DME (3 mL) was added benzofuran boronic acid (132 mg, 0.802 mmol), followed by Pd(PPh3)4 (35 mg, 0.03 mmol) and K2CO3 (145 mg, 1.05 mmol). The reaction mixture was stirred at 80 C. for 16 h. The mixture was filtered and washed with CH2Cl2 (10 mL). The solvent was evaporated under reduced pressure and purified by column chromatography using 0 to 80% EtOAc in hexane over 40 min as eluting gradient to afford 16a (38 mg, 40%) as a yellowish powder. MS (ES) m/z 257 [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, 19755-53-4, 2-Bromo-3-nitropyridine.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293336; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1180132-17-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1180132-17-5 as follows.

Add to the microwave reaction flask7- [2-Chloro-5-fluoropyrimidin-4-yl) -5-fluoro-2,3-dihydro-1H-benzo [d] pyrrole [1,2-a] imidazole (100 mg, 0.33 mmol, Example 11 Preparation),5 – ((4-ethylpiperazin-1-yl) methyl) pyridin-2-amine(7 mg, 0.33 mmol, prepared in second step), sodium tert-butoxide (64 mg, 0.66 mmol), Pd2 (dba) 3 (30 mg, 0.033 mmol)XantPhos (38 mg, 0.066 mmol) and anhydrous 1,4-dioxane (5 mL).The mixture was microwave reacted at 150 C for 1 hour.Cooled to room temperature, extracted with water (10 mL), and ethyl acetate (40 mL x 3).The organic phases were combined, washed with saturated sodium chloride solution (40 mL x 2), dried over anhydrous sodium sulfate,Filtered, concentrated under reduced pressure. The residue was purified by column chromatography (DCM / MeOH = 10: 1)The resulting residue was purified to give the title compound (15 mg, yellow solid)Yield 9.3%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1180132-17-5, its application will become more common.

Reference:
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 944896-42-8, 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 944896-42-8, name is 6-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

[Step a] To a mixed solution of compound 1 (210 mg, 533 mumol) obtained in Reference Example 65, Step b, in dioxane (4.00 mL) and water (500 muL) were added potassium carbonate (170 mg, 1.23 mmol), compound 2 (, 100 mg, 415 mumol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (30 mg, 42.3 mumol), and the mixture was heated in a nitrogen atmosphere under microwave radiation at 150C, and stirred for 1 hr. The reaction solution was allowed to cool to room temperature, 1 M-hydrochloric acid (3.5 mL) was added, and the mixture was extracted with a tetrahydrofuran and ethyl acetate mixed solution (1:1). The aqueous layer was further extracted with a tetrahydrofuran and chloroform mixed solution (1:1), and the organic layers were combined, washed with saturated brine, and concentrated. The residue was subjected to solid phase extraction purification with a cation exchange resin column (Waters, PoraPak, RxnCX), and the obtained solid was suspended and washed in ethyl acetate (2.00 mL) to give compound 3 (70.0 mg, 39.4%).

According to the analysis of related databases, 944896-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; TAKAHASHI, Taichi; UMINO, Akinori; IIJIMA, Daisuke; TAKAMATSU, Hisayuki; (173 pag.)EP3135667; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1123194-98-8, 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)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, Recommanded Product: 1123194-98-8, blongs to pyridine-derivatives compound. Recommanded Product: 1123194-98-8

DMF (52mL) was added to 6-Bromo-2-methoxy-3-(4-methyl-l H- imidazol-1-yl)pyridine (13.Og, 48.5mmol) and the tert-Butyl 2- acryloylhydrazinecarboxylate (9,9g, 53.3mmol) at room temperature under nitrogen atmosphere, And the mixture was stirred at 50C for 10minutes, Tri(o-tolyl)phosphine (885mg, 2.90mmol), Palladium (II) acetate (327mg, 1.45mmol) and N,N- diisopropylethylamine (12.7mL, 72.7mmol) were added to the mixture, and the reaction mixture was stirred at 100C for 4hours. The reaction mixture was cooled to room temperature and filtrated through Celite. The residue was washed twice with DMF (6mL). Water (104mL) was added dropwise to the filtrate at room temperature over lOminutes. The mixture was stirred at room temperature for l5hoursAfter the mixture was filtrated, the residue was washed with water/DMF =2; 1(3OmL) and MTBE (3OmL). The obtained solid was suspended in MTBE (5OmL) at room temperature for 2hours, filtrated and dried under the reduced pressure to obtain the title compound (15.8g, 87% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1123194-98-8, 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; NAKAMURA, Taiju; MATSUDA, Masaaki; HU, Yongbo; HASEGAWA, Daiju; HOSHINO, Yorihisa; INANAGA, Kazato; ISOMURA, Minetaka; SATO, Nobuaki; YOSHIZAWA, Kazuhiro; MONIZ, George A.; WILKIE, Gordon D.; FANG, Francis G.; NISHIKAWA, Yoshihiro; WO2010/25197; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1231930-25-8, 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.1231930-25-8, name is 1-((6-Bromopyridin-3-yl)methyl)-4-ethylpiperazine, molecular formula is C12H18BrN3, molecular weight is 284.2, as common compound, the synthetic route is as follows.

A solution of 1- (6-bromo-pyridin-3-ylmethyl) -4-ethyl-piperazine (960 mg, 3.38 mmol) in anhydrous tetrahydrofuran (8 mL)Was added 2- (dicyclohexylphosphino) biphenyl (120 mg, 0.338 mmol)Tris (dibenzylideneacetone) dipalladium (154 mg, 0.169 mmol).Lithium hexamethyldisilazide (4.06 mL, 1 M, 4.06 mmol) was slowly added under nitrogen.The reaction flask was heated to 65 C,After 20 minutes the reaction flask was cooled to room temperature,50 mL of ethyl acetate was added,30mL water,Mixed after the liquid,The aqueous layer was again added with 30 mL of ethyl acetate,Liquid separation,Combined organic layer,Dried over anhydrous sodium sulfate and evaporated to dryness as a pale brown solid.The product of formula V-1 (670 mg) was purified by column chromatography,As a pale yellow solid.

The chemical industry reduces the impact on the environment during synthesis 1231930-25-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Zhang, Yinsheng; Liu, Yingshuai; Li, Li; Miao, Lei; Xu, Tongjie; Liu, Haiyan; Ma, Xueqin; Yu, Sen; Xu, Hongjiang; (49 pag.)CN106467517; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 162102-79-6, Dimethyl 4-bromopyridine-2,6-dicarboxylate, 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, Computed Properties of C9H8BrNO4, blongs to pyridine-derivatives compound. Computed Properties of C9H8BrNO4

In a sealed tube, a mixture of 1 (2.74 g, 10 mmol)and (S)-phenylalaninol (3.78 g, 25 mmol) in methanol (10 mL) was stirred at 115 C for 12 h. After cooling to ambient temperature, the crude product was poured into crushed ice (100 g), stirred for15 min, filtered, washed with water (20 mL 3) and the residues was dried under vacuum. The white product was used for the next step without further purification (4.50 g, 88%). 1H NMR (400 MHz,CDCl3): d 8.43 (s, 2 H), 7.94 (d, J 8 Hz, 2 H), 7.32e7.21 (m, 10 H),4.40e4.32 (m, 2 H), 3.83e3.74 (m, 4 H), 3.06e2.96 (m, 4 H), 2.59 (br,2 H). 13C NMR (150 MHz, CDCl3): d 162.6, 149.7, 137.5, 136.4, 129.4,128.8, 128.5, 126.9, 63.6, 53.1, 37.0. HRMS (MALDITOF) calcd forC25H27BrN3O4 [M H] 512.1179, found 512.1186.

The synthetic route of 162102-79-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Ya-Qi; Pan, Yao; Gao, Wan-Qing; Wu, Yuan; Liu, Chun-Hua; Zhu, Yuan-Yuan; Tetrahedron; vol. 75; 28; (2019); p. 3809 – 3814;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem