Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 271-47-6, 1H-Pyrazolo[3,4-c]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, HPLC of Formula: C6H5N3, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5N3

To a solution of 1H-pyrazolo[3,4-c]pyridine (4.0 g, 33.6 mmol, 1.0 eq.) in DMF(40 mL) were added K2C03 (9.3 g, 100.8 mmol, 3.0 eq.), ?2 (7.9 g, 33.6 mmol, 1.0 eq.). Theresulting mixture was stirred at r.t. for 3 hr, then diluted by H20 and filtered. The collectedsolid was dried to give 3-iodo-1H-pyrazolo[3,4-c]pyridine (6.0 g, 73.0 %).

The synthetic route of 271-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHAMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (241 pag.)WO2017/98328; (2017); A2;,
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. 102830-75-1, name is 3-Bromo-5-chloro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Bromo-5-chloro-2-methoxypyridine

When the above procedure was repeated using 3-bromo-5-chloro-2-methoxypyridine, the product obtained was 5-chloro-2-methoxypyridine-3-carboxaldehyde melting at about 93-96 C.

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, 102830-75-1, 3-Bromo-5-chloro-2-methoxypyridine.

Reference:
Patent; Merrell Dow Pharmaceuticals Inc.; US4588733; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74409-42-0 ,Some common heterocyclic compound, 74409-42-0, molecular formula is C8H11NO, 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.

2,3,5-trimethylpyridine 1-oxide (1.38 kg, 10.1 mol) was charged into 98% sulfuric acid (4.93 kg, 49.3 mol). 97% nitric acid (1.44 kg) was added dropwise to the solution over 50 minutes, and the solution was then heated for 4 hours at 85C. The reaction solution was charged into a mixture of ammonium hydrogencarbonate (10.6 kg) and water (9.0 L), and the resultant mixture was extracted with ethyl acetate (3.0 L × 3). The resultant organic layer was concentrated and then dried overnight under vacuum to obtain 1.50 kg of the title compound.

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. 74409-42-0, 2,3,5-trimethylpyridine 1-oxide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1875911; (2008); 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.37669-64-0, name is 5-Bromo-3-pyridinemethanol, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) cooled to 0 C. was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature over night. The mixture was poured onto ice/water (20 mL), basified with NaOH conc. (8 mL) and extracted with EtOAc (2×50 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtOAc-Heptane gradient to give the title compound (3.08 g, 93%) as a white solid. MS: 206.0, 207.9 (M+H+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,37669-64-0, 5-Bromo-3-pyridinemethanol, 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

Reference of 132330-98-4, 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 132330-98-4, name is 3-(Benzyloxy)-2-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

TFA (30 mL) was placed in the round-bottom flask equipped with a magneticstirred, and the reaction mixture was cooled to 0 C under Ar. Then, tert-butyl(mesitylsulfonyl)oxycarbamate (6.34 g, 20.00 mmol) was added portionwise over 5 mm, and the reaction mixture was stirred at 0 C for 1 h under Ar. Afterwards, the reaction mixture was quenched with ice water (100 mL), producing white solid. The reaction mixture was diluted with cold water (150 mL), the solid was filtered off, and was washedwith cold water until pH7.0. The obtained solid was dissolved in DCM (75.0 mL), and was stirred with Na2SO4 at 0 C for 15 mm to remove water. Afterwards, Na2SO4 was removed by filtration, and the DCM solution was added to a cooled (ice bath) solution of 3-(benzyloxy)-2-bromopyridine (4.41 g, 16.1 mmol) in DCM (25 mL). The reaction mixture was stirred at 0 C for 2 h. Then, ice bath was removed, and the reaction mixturewas allowed to reach rt and was stirred at this temperature for 1 h. Solvent was removed under reduced pressure, the residue was dissolved in DMF (100 mL), then methyl propiolate (2.86 mL, 32.1 mmol) and K2C03 (6.66 g, 48.2 mmol) were added sequentially. The obtained suspension was stirred at rt for 16 h. The reaction mixture was diluted with EtOAc (500 mL), washed with water (3×250 mL), brine (1×250 mL), dried(Na2504) and filtered. The residue was purified by flash chromatography to give Intermediate 47 (0.88 g, 15% yield) as an off-white solid. MS(ESI) m/z: 260.8 (M+H)?H NMR (300MHz, CDC13) oe ppm 8.45 (s, 1H), 8.15 (d, J=9.6 Hz, 1H), 7.48-7.16 (m, 6H), 5.24 (s, 2H), 3.91 (s, 3H).

According to the analysis of related databases, 132330-98-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 717106-69-9 , The common heterocyclic compound, 717106-69-9, name is Methyl 2-(6-chloropyridin-3-yl)acetate, molecular formula is C8H8ClNO2, 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.

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 2-(6-chloropyridin-3-yl)acetate (1.86 g, 10.0 mmol, 1.00 equiv), toluene (50 mL), Cs2CO3 (10.0 g, 30.0 mmol, 3.00 equiv), 1-benzylpiperazine (2.11 g, 12.0 mmol, 1.2 equiv), and RuPhosPd (0.39 g, 0.05 equiv). The resulting solution was stirred for 10 hours at 100 C. in an oil bath. The reaction mixture was cooled to room temperature. The reaction was then quenched by the addition of water (50 mL). The resulting solution was extracted with ethyl acetate (100 mL*2), and the organic layers were combined. The resulting mixture was washed with brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (v:v=1/3). This resulted in 1.1 g (32%) of methyl 2-[6-(4-benzylpiperazin-1-yl)pyridin-3-yl]acetate as a yellow solid.

The synthetic route of 717106-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arvinas Operations, Inc.; Genentech, Inc.; Crew, Andrew P.; Wang, Jing; Berlin, Michael; Dragovich, Peter; Chen, Huifen; Staben, Leanna; US2019/300521; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 819069-57-3, Adding some certain compound to certain chemical reactions, such as: 819069-57-3, name is 3-Bromo-6-methoxy-2,4-dimethylpyridine,molecular formula is C8H10BrNO, 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 819069-57-3.

Preparation Example 24 Synthesis of (6-methoxy-2,4-dimethylpyridin-3-yl)boronic acid 3-bromo-6-methoxy-2,4-dimethylpyridine (150 mg) was added to THF (3 mL). The solution was cooled to -78 C., and n-butyllithium (1.63 M solution in n-hexane, 0.468 mL) was added, followed by stirring at the same temperature for 30 minutes. Trimethyl borate (0.108 mL) was added to the reaction mixture, and the mixture was stirred at -78 C. for 10 minutes and at room temperature for 50 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the reaction mixture was concentrated under reduced pressure. THF was distilled off. The resulting residue was filtered. The solid collected by filtration was washed with water and n-heptane to give the title compound (41 mg). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.31 (s, 3H), 2.48 (s, 3H), 3.89 (s, 3H), 4.77 (brs, 2H), 6.35 (s, 1H).

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. 819069-57-3, 3-Bromo-6-methoxy-2,4-dimethylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 174669-74-0, 2-Fluoropyridin-3-ol, 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, 174669-74-0, blongs to pyridine-derivatives compound. Formula: C5H4FNO

To a stirred solution of 2-fluoropyridin-3-ol (J. Labelled Cou7npound. Radioplzann., 1998, 41, 451) (3.81 g, 33.7 mmol) and sodium acetate (2.76 g, 33.7 mmol) in acetic acid (30 mL) was added bromine (1.74 mL, 33.7 mmol) at 0C, and the mixture was stirred at room temperature for 3.5 hours. The mixture was poured onto ice-aq. sodium hydroxide and extracted with ethyl acetate. The combined organic layer was dried and evaporated to afford the titled compound as a yellow solid (4.67 g, 72 %). ‘H NMR (270MHz, DMSO-d6) 8 = 7.29 (d, J = 8.2 Hz, 1H), 7.28 (s, 1H), 7.23 (d, J = 8.2 Hz, 1H) ppm. MS (EI) ; M+=191, 193

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,174669-74-0, its application will become more common.

Reference:
Patent; PFIZER JAPAN, INC.; PFIZER INC.; WO2005/35522; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1195-59-1, 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 1195-59-1 as follows.

Example 15 2,6-Bis(bromomethyl)pyridine. To pyridine-2,6-diyldimethanol (2 g, 14 mmol) was added 60% HBr (15 mL) slowly. The reaction was heated at 125 C. for 6 h then cooled to room temperature. The resulting residue was dissolved in H2O (50 mL) to give a yellow solution. To this solution was added saturated NaHCO3 to pH 8. The resulting aqueous solution was extracted with CH2Cl2 (4×50 mL), and the combined organic layers were dried over Na2SO4. The solvent was removed by rotary evaporation, and the resulting material was purified by flash column chromatography (EtOAc/hexanes, 1:9-1:4) to yield 2,6-bis(bromomethyl)pyridine (3.5 g, 96%) as a white solid: 1H NMR (500 MHz, CDCl3) delta 4.53 (s, 4H), 7.36-7.38 (d, J=8.0 Hz, 2H), 7.68-7.71 (dd, J=7.5, 8.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) delta 33.8, 123.1, 138.4, 157.0; LC-TOF (M+H+) calcd for C7H8Br2N 263.90235, found 263.90193.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1195-59-1, its application will become more common.

Reference:
Patent; Silverman, Richard B.; Xue, Fengtian; US2010/203613; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 113118-81-3, 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. 113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, 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.

To a solution of 5-bromonicotinaldehyde (XXV) (2.05 g, 11.0 mmol) in MeOH (85 mL) was added NaB (832 mg, 21.99 mmol). The reaction was stirred at room temperature for 1 h. The reaction was quenched with saturated aqueous NH4CI (5 mL). The reaction was concentrated under vacuum and the residue was partitioned between saturated aqueous NLLCl/EtOAc. The organic layer was separated, washed with water, brine, dried over MgS04 and concentrated under vacuum to yield crude (5-bromopyridin-3-yl)methanol (XLV) as a golden oil (1.54 g, 8.2 mmol, 74% yield). The product was used without further purification. ESIMS found for C6H6BrNO mlz 188 (M+H).

According to the analysis of related databases, 113118-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC; DESHMUKH, Vishal; MURPHY, Eric Anthony; HOOD, John; (232 pag.)WO2018/75858; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem