Tag: M.W:200-300

Application of 60010-03-9, 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. 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

6-chloro-2-(4,4-difluoro-1 -piperidyl)-4-methyl-3-nitro-pyridine (Intermediate com- pound)A solution of 2,6-dichloro-4-methyl-3-nitropyhdine (4.5g;21.7 mmol), 4,4- Difluoropiperidine (3.97g; 1.1 eq) and TEA (12ml; ca.4eq) in MeCN (30ml) was stirred at rt over night after which the reaction mixture was quenched with sat.NaHCOs(aq) solution and extracted with EtOAc (3x 5OmL). The combined or- ganic. were washed with brine, dried over Na2SO4(s), filtered and evaporated in vacuo to give 6.27g yellow solid (90% pure title compound)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60010-03-9, its application will become more common.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; MATTSSON, Cecilia; SOTT, Richard; STRØBAeK, Dorte; WO2010/122064; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 26163-03-1, 3-Bromo-5-chloropyridin-2-amine, 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, HPLC of Formula: C5H4BrClN2, blongs to pyridine-derivatives compound. HPLC of Formula: C5H4BrClN2

Under nitrogen protection,Acetonitrile (100 mL) was added sequentially to a 500 mL three-necked flask,Elemental iodine (48.9 g, 192.8 mmol)Cuprous iodide (23.9 g, 125.3 mmol) andTert-butyl nitrite (14.9 g, 144.6 mmol)2-Amino-3-bromo-5-chloropyridine (20.0 g, 96.4 mmol) was slowly added under ice-cooling to react at 60 C for 2 h.After completion of the reaction, water (45 mL) was added,The filter cake was extracted with ethyl acetate (45 mL x 1) and the filtrate was extracted with ethyl acetate (200 mL x 2)The phases were washed with saturated aqueous sodium thiosulfate solution (110 mL x 2), dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.A small amount of methanol beating, filter, filter cake after drying 2 – iodo-3-bromo-5-chloropyridine white solid 21.9g, the yield of 71.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26163-03-1, 3-Bromo-5-chloropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Guizhou University; Zhao, Chunshen; Chai, Huifang; Zhou, Zhixu; Le, Yi; Liu, Li; Teng, Minggang; Huang, Zhuyan; (5 pag.)CN106467488; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 942473-59-8, 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 942473-59-8 as follows.

2,5-Dibromopyridine-4-carboxylic acid (25.0 g) is dissolved in MeOH (400 ml.) and cone, sulfuric acid (5 ml.) is added dropwise at ambient temperature. The reaction is heated to reflux and stirred for 16 h. After cooling to ambient temperature the solution is concentrated under reduced pressure and partitioned between EtOAc and aq. sat. NaHCO-3. The organic phase is washed with aq. sat. NaHCO-3, dried over Na2S04, solid parts are removed by filtration and concentrated under reduced pressure. Column chromatography of the resulting crude product (ISCO-CombiFlash Rf, cyclohexane/EtOAc) yields the title compound (23.8 g, yield 91 %) as a colorless oil. (2134) H NMR (400 MHz, DMSO-c 6): delta = 8.77 (s, 1 H), 8.01 (s, 1 H), 3.91 (s, 3H) ppm; MS (ESI) m/z 295.9 [M + H+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,942473-59-8, its application will become more common.

Reference:
Patent; BASF SE; VOGT, Florian; WITSCHEL, Matthias; SEISER, Tobias; LOPEZ CARRILLO, Veronica; SEITZ, Thomas; KRAEMER, Gerd; KREUZ, Klaus; NEWTON, Trevor William; REINHARD, Klaus; SCHACHTSCHABEL, Doreen; TRESCH, Stefan; (109 pag.)WO2018/19758; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-10-3, 6-Chloro-5-nitronicotinic acid, 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: C6H3ClN2O4, blongs to pyridine-derivatives compound. Formula: C6H3ClN2O4

General procedure: A solution of compound 4 and different primary and secondary amines were stirred at rt for 1h, followed by extraction with EtOAc. The extract was then washed with 1N HCl, water, and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography (hexane/EtOAc=2:1) to give product 6 as a solid.4.2.4.4 6-[4-(2-Methoxyphenyl)piperazin-1-yl]-5-nitronicotinic acid (6d) Procedure A was used with compound 5 (100 mg, 0.5 mmol) and 1-(2-methoxyphenyl)piperazine (193 mg, 1.0 mmol) to afford product 6d as a yellow solid (138 mg, 77%). 1H NMR (300 MHz, CDCl3) delta: 8.92 (d, J = 1.8 Hz, 1H), 8.74 (d, J = 1.8 Hz, 1H). 7.08-7.03 (m, 1H), 6.94-6.89 (m, 3H), 3.90 (s, 3H), 3.82 (t, J = 4.8 Hz, 4H), 3.18 (t, J = 4.8 Hz, 4H). ESI-MS: m/z (357, MH-).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7477-10-3, 6-Chloro-5-nitronicotinic acid, and friends who are interested can also refer to it.

Reference:
Article; Zhao, Chao; Yang, Su Hui; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kyung-Tae; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 985 – 995;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 116855-03-9, Adding some certain compound to certain chemical reactions, such as: 116855-03-9, name is 3-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine,molecular formula is C7H6BrN3, 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 116855-03-9.

3-bromo-1-methyl-pyrazolo[3,4-b]pyridine (100 mg, 0.472 mmol) is dissolved in toluene (5 mL) and tributyl(1-ethoxyvinyl)tin (187 mg, 0.519 mmol) and tetrakis(triphenylphosphine) palladium(0) (54 mg, 0.047 mmol) are added to the solution and the reaction is refluxed for 2 h. Volatiles are evaporated under reduced pressure and the resulting residue is suspended in THE/aqueous 2M HCI 1:1 andstirring is continued for lh. The reaction mixture is basified with Na2CO3 saturated solution, and extracted with ethyl acetate. The organic layer is dried, evaporated and the resulting residue is purified by flash chromatography (eluent 0-100% EtOAc/Cyclohexane) to give the title compound (70 mg, 85 %)UPLC-MS (Method 2): R = 0.78 mmMS (ESI pos): m/z = 176 (M+H)+

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. 116855-03-9, 3-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; WO2014/184275; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 84487-15-0, 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 84487-15-0, name is 2-Bromo-5-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

4-Amino-5-nitropicolinonitrile (Compound 64) A solution of 2-bromo-5-nitropyridin-4-amine (135 mg, 0.619 mmol) and copper cyanide (67 mg, 0.743 mmol) in DMA was heated to 200 C. for 1 h using a microwave reactor. The reaction mixture was partitioned between water and EtOAc and filtered over celite. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by combiflash SiO2 chromatography using (0-50% EtOAc-hexanes) to give 4-amino-5-nitropicolinonitrile (70 mg, 69%) as a pale brown solid. 1H-NMR (400 MHz, CD3OD) delta ppm 9.07 (s, 1H), 7.37 (s, 1H); ESI-MS: m/z 164.77 (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 84487-15-0, 2-Bromo-5-nitropyridin-4-amine.

Reference:
Patent; Stingray Therapeutics, Inc.; Vankayalapati, Hariprasad; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (117 pag.)US2020/39979; (2020); 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. 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H8BrNO2

Into a vial was weighed methyl 5-bromo-4-methylpicolinate (1.00 g, 4.35 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (181 mg, 0.217 mmol), bis(pinacolato)diboron (1.21 g, 4.78 mmol), and potassium acetate (1.28 g, 13.0 mmol). Under nitrogen, anhydrous 1,4-dioxane (11 mL) was added and the vial was sealed. The reaction mixture was stirred at 100 C. for 18 h. After cooling to rt, the reaction mixture was concentrated and the residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10) to afford 756 mg of crude aryl pinacolboranate intermediate (contaminated with pinacolborane by 1H NMR). Combining this intermediate (323 mg, ?1.17 mmol) with (+-)-(1S,2S)-N-(8-(bis(2,4-dimethoxybenzyl)amino)-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (500 mg, 0.777 mmol), chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (32.8 mg, 0.0389 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (18.9 mg, 0.0389 mmol), and potassium phosphate tribasic monohydrate (554 mg, 2.33 mmol) in a vial, tetrahydrofuran (3.9 mL) and water (0.7 mL) were added under nitrogen and the vial was sealed and stirred at 80 C. for 19 h. The reaction mixture still contained starting material and so an equal aliquot of catalyst, ligand and water, as well as potassium phosphate tribasic monohydrate (184 mg, 0.777 mmol) and crude aryl pinacolboranate (215 mg, ?0.77 mmol) were added and stirred at 80 C. for 3 days. The mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10). The crude compound thus obtained was a yellow oil that contained the product according to HPLC-MS.

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, 886365-06-6, Methyl 5-bromo-4-methylpicolinate.

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

Application of 109306-86-7, 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.109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.

Add 2g of magnesium turnings, one iodine, a small amount of tetrahydrofuran (THF), and a small amount of 2-(2-bromophenyl)pyridine in a 500ml three-necked flask.After the reaction was initiated, 200 ml of a solution of 2-(2-bromophenyl)pyridine (19 g) in tetrahydrofuran (THF) was slowly added dropwise.After refluxing until the magnesium dust disappeared, 15 g of a solution of compound 3 in THF was added dropwise, 100 ml.The reflux reaction was continued for 8 hours, then the temperature was lowered to room temperature, and 2N hydrochloric acid was added to quench the reaction.The solvent was evaporated under reduced pressure, and 300 ml of acetic acid was added to the obtained solid, and the mixture was heated to reflux for 2 hours.The solvent was removed by filtration at room temperature.After the obtained white solid was dissolved in 100 THF, an equal amount of methanol was slowly added.The white solid product was precipitated to 16.3 g, and the yield was 72.6%.

Statistics shows that 109306-86-7 is playing an increasingly important role. we look forward to future research findings about 2-(2-Bromophenyl)pyridine.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Liu Kaipeng; Yang Yan; Yang Dandan; Zhang Hongke; Gao Renxiao; (25 pag.)CN108948030; (2018); A;,
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. 183483-29-6, name is 2-(2-Bromopyridin-4-yl)acetic acid, the common compound, a new synthetic route is introduced below. Product Details of 183483-29-6

2-(2-Bromopyridin-4-yl)acetic acid (5 g, 23.1 mmol), benzene (40.5 ml) and MeOH (5.8 ml) were added to a 250 mL flask, thentrimethylsilyldiazomethane (11.6 ml, 23.1 mmol, 2 M) was added dropwise over 5 mm. The reaction was concentrated in vacuo. Silica gel chromatography using a hexanes/EtOAc gradient (0-100%) afforded the title compound.

The synthetic route of 183483-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAN, Xiaoqing; WHITEHEAD, Alan; RAGHAVAN, Subharekha; GROEPER, Jonathan; GUO, Jian; ZHANG, Yong; WO2015/88885; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 717843-51-1 ,Some common heterocyclic compound, 717843-51-1, molecular formula is C7H8BrNO, 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.

General procedure: To a mixture of the appropriate amine E (1 eq), the appropriate halide (1.05 to 1.2 eq) and sodium ferf-butoxide (2 eq) in toluene (3 mL/mmol) under N , was added BINAP (0.2 eq) and Pd2(dba)3 (0.1 eq). The rxn mixture was flushed with N , heated to a given temperature in a sealed vial and stirred for a given time (see Table 27). It was partitioned between water and EtOAc and the org. phase was washed with brine, dried over MgSCh and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc.

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. 717843-51-1, 3-Bromo-2-methoxy-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (266 pag.)WO2019/137927; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem