Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 10201-73-7, 2-Amino-4-methoxypyridine, 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: C6H8N2O, blongs to pyridine-derivatives compound. COA of Formula: C6H8N2O

General procedure: To the solution of Acid SM-IX (70 mg, 0.20 mmol, 100 mol-%) in dry DMF (2 ml) under nitrogen atmosphere was added i-hydroxybenzotriazole hydrate (HOBt) (60 mg, 0.45 mmol, 220 mol-%), i-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (EDCI) (86 mg, 0.45 mmol, 220 mol-%) and 3- amino-6-methoxypyridazine (51 mg, 0.41 mmol, 200 mol-%). The reaction mix-ture was stirred at + 50 C for 3.5 hours. Water (3 ml) was added to the reaction mixture. The solid precipitate was filtered and washed several times with water and finally with heptane to yield 56 mg of crude product. Purification was done by flash chromatography. Amount of product compound 3 was 36 mg.1H-NMR (200 MHz, DMSO-d6): 0.98 (5, 3H), 1.20-2.47 (m, 16H),2.60-2.97 (m, 2H), 3.98 (5, 3H), 6.89-7.06 (m, 1H), 7.08-7.21 (m, 2H), 7.25 (d,1H), 8.26 (d, 1H), 10.94 (brs, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10201-73-7, 2-Amino-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; FORENDO PHARMA LTD; HIRVELAe, Leena; HAKOLA, Marjo; LINNANEN, Tero; KOSKIMIES, Pasi; STJERNSCHANTZ, Camilla; (182 pag.)WO2018/224736; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65515-32-4 ,Some common heterocyclic compound, 65515-32-4, molecular formula is C8H8ClNO3, 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.

To a solution of 6-Chloro-2-methoxy-nicotinic acid methyl ester (18.5.0 g, 0.092 mol) in 50 mL of NMP was added p-methoxybenzylamine (19.0 g, 0.14 mol) and triethylamine (10.Og, 0.1 mol). The mixture was heated to 70 0C for 4 h, cooled and diluted with water and extracted with ethyl acetate, washed with water, brine, dried with sodium sulfate, and evaporated to get an oil which was precipitated with ethylacetate/hexane mixture (1 :1). This was then filtered and dried to yield 15 g (60 %) of the target compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65515-32-4, its application will become more common.

Reference:
Patent; SCIOS, INC.; WO2006/112828; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 86604-79-7, 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 86604-79-7, name is 2,3,5-Trimethyl-4-nitropyridine 1-oxide. This compound has unique chemical properties. The synthetic route is as follows.

The 2,3,5-trimethyl-4-nitropyridine1-oxide (13.4 g, 73.6 mmol) obtained in the step (11c) was added to acetyl chloride (80 ml, 1,125 mmol) at -30 C. in a nitrogen atmosphere. The mixture was stirred at -30 C. to room temperature for 4 hours and 20 minutes. After the reaction mixture was concentrated, the residue was subjected to silica gel column chromatography (NH silica gel: 300 g, elution solvent: heptane, heptane/ethyl acetate=50/50, ethyl acetate, ethyl acetate/methanol=10/1) to obtain fractions containing a pure product of the title compound and fractions containing a crude product of the title compound. The fractions containing a crude product of the title compound was concentrated. The residue was suspended in ethyl acetate and the resulting precipitate was collected by filtration, washed with ethyl acetate and diethyl ether to obtain the title compound (Lot A, 1.58 g) as a white solid. The filtrate was concentrated. The residue was dissolved in chloroform and washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was suspended in diethyl ether. The resulting precipitate was collected by filtration, washed with diethyl ether to obtain the title compound (Lot B, 2.69 g) as a pale brown solid. The fractions containing a pure product of the title compound were concentrated. The residue was dissolved in chloroform, washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous sodium sulfate, filtered and concentrated to obtain the title compound (Lot C, 6.56 g) as a pale white solid. The yield of the obtained title compounds of 3 lots was 85.7% in total. Lot A: 1H NMR(400 MHz, DMSO-d6) deltappm; 2.24(3H, s), 2.35(3H, s), 2.39(3H, s), 8.25(1H, s). Lot B: 1H NMR(400 MHz, DMSO-d6) deltappm; 2.24(3H, s), 2.35(3H, s), 2.39(3H, s), 8.25(1H, s). Lot C: 1H NMR(400 MHz, DMSO-d6) deltappm; 2.24(3H, s), 2.35(3H, s), 2.39(3H, s), 8.25(1H, s).

According to the analysis of related databases, 86604-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; US2007/10542; (2007); 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. 20265-35-4, name is 2-Methoxy-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6N2O3

Method 4 Synthesis of 7-methoxy-1H-pyrrolo[2,3-c]pyridine (Intermediate 5) A solution of R-4 (500 mg, 3.24 mmol) in anhydrous THF (20 mL) is cooled to -78° C. and vinylmagnesium bromide (9.73 mL of a 1 M solution in THF, 9.73 mmol) added. The reaction is stirred at -20° C. for 6 h then quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The organic phase is concentrated in vacuo and the crude material purified by flash chromatography (SiO2, 2percent to 10percent MeOH in DCM) to give the title intermediate I-5 (100 mg) m/z 148.9 [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, 20265-35-4, 2-Methoxy-3-nitropyridine.

Reference:
Patent; BARTOLOZZI, Alessandra; CHEN, Zhidong; DINES, Jonathon Alan; LO, Ho Yin; LOKE, Pui Leng; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee M.; US2013/196967; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 94220-45-8, name is 5-Chloro-1H-pyrazolo[4,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H4ClN3

10786] To a suspension of sodium hydride (94 mg, 2.3 mmol, 60% in mineral oil) in DMF (4.0 mE) was added dropwise a solution of 5-chioro-1 H-pyrazolo[4,3-b]pyridine (0.30 g, 2.0 mmol, J&W Pharmlab) in DMF (1.0 mE). The mixture was stirred for 10 minutes, then benzyl bromide (0.244 mE, 2.05 mmol, Aldrich) was added. Afier 70 minutes, the mixture was quenched by the addition of water and the product was extracted with EtOAc. The combined extracts were washed with water, followed by brine, dried over sodium sulfate, filtered, and concentrated. Flash chromatography, eluting with a gradient from 0-20% EtOAc in hexanes afforded two isomeric products: Peak 1 (first to elute, 1-ben- zyl-5-chloro-1 H-pyrazolo[4,3-b]pyridine): 0.21 g, 44% yield. Peak 2 (second to elute, 2-benzyl-5-chloro-2H-pyra- zolo[4,3-b]pyridine): 0.10 g, 21% yield.Peak 1 (first to elute, 1-benzyl-5-chloro-1H-pyrazolo[4,3-b] pyridine): ?H NMR (500 MHz, CDC13) oe 8.19 (d, J=0.8 Hz, 1H), 7.56 (dd, J=8.8, 0.7 Hz, 1H), 7.38-7.27 (m, 3H), 7.22 (d,J=8.8 Hz, 1H), 7.18 (dd, J=7.7, 1.5 Hz, 2H), 5.59 (s, 2H);LCMS (M+H): 244.1, 246.1.Peak 2 (second to elute, 2-benzyl-5-chloro-2H-pyrazolo[4,3-b]pyridine): ?H NMR (500 MHz, CDC13) oe 8.07 (d, J=0.8 Hz,1H), 8.00 (dd, J=9.0, 0.8 Hz, 1H), 7.41-7.33 (m, 3H), 7.29(dd, J=7.6, 1.7 Hz, 2H), 7.19 (d, J=9.0 Hz, 1H), 5.60 (s, 2H);LCMS (M+H): 244.1, 246.1.

With the rapid development of chemical substances, we look forward to future research findings about 94220-45-8.

Reference:
Patent; Incyte Corporation; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; US2015/175604; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65515-28-8, Methyl 2,6-dichloronicotinate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A 250 mL eggplant flask was sequentially charged with methyl 2,6-dichloronicotinate (4.12g, 20 mmol), [1,1?-biphenyl]-4-phenol (3.40 g, 20 mmol), and 24 mL of N, N-dimethylformamide for dissolving them. Triethylamine (3.8 mL,26 mmol) was added dropwise under stirring at room temperature, and after completion of the dropwise addition, triethylenediamine (336 mg, 3 mmol) was added. The mixture was stirred at room temperature for 4-5 hours and the solutionchanged from clear to turbid. Thin layer chromatography [V (petroleum ether) / V (ethyl acetate) = 6/1] detected thatmost of the raw material disappeared. Then, 1.30 mL of HOAc, 25 mL of isopropanol and 15 mL of ice water weresequentially added while the solution changed from turbid to clear, and stirred at room temperature for 0.5 hour. 40mLof water was slowly dropwise added, and after completion of the dropwise addition, stirred at room temperature for 2hours. A large number of white solid precipitated and was filtered. The filter cake was washed with a mixed solution ofisopropyl alcohol / water = 1: 1 and dried under vacuum at 50 C for 8 hours to obtain 5.66 g of methyl 6-([1,1?-biphenyl]-4-oxo)-2-chloronicotinate as a solid, 83.24%

The synthetic route of 65515-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenyang Sunshine Pharmaceutical Co., Ltd.; ZHOU, Yunlong; CAI, Suixiong; WANG, Guangfeng; JIAO, Lingling; MIN, Ping; JING, Yu; GUO, Ming; (44 pag.)EP3275881; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 65515-28-8, 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.65515-28-8, name is Methyl 2,6-dichloronicotinate, molecular formula is C7H5Cl2NO2, molecular weight is 206.03, as common compound, the synthetic route is as follows.

step 1 (S ) -6-chloro-2- [1- (4-fluorophenyl) ethylamino] methyl nicotinatewas dissolved 2,6-dichloro-nicotinic acid methyl ester 5.0 g N, the N- dimethylformamide 50 ml, (S) – (-) – 1- (4-fluorophenyl) ethylamine 4.39 g, N, N-diisopropylethylamine 6.27g and 4-dimethylaminopyridine 150mg was added, and stirred for 24 hours at 60 C..The reaction mixture was cooled, diluted with ethyl acetate, washed successively with water and saturated brine, and dried over magnesium sulfate.Under reduced pressure, the solvent was distilled off, the resulting residue was purified by silica gel column chromatography to give the title compound 2.83g as a white powder.

Statistics shows that 65515-28-8 is playing an increasingly important role. we look forward to future research findings about Methyl 2,6-dichloronicotinate.

Reference:
Patent; NIPPON SHINYAKU COMPANY LIMITED; FUJIHARA, HIDETAKA; ASAKI, TETSUO; HORI, KATSUTOSHI; NAITO, HARUNA; (146 pag.)JP5668756; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 588729-99-1, 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.588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, molecular formula is C5H4BrClN2, molecular weight is 207.4557, as common compound, the synthetic route is as follows.

(1) 5-bromo-3-amino-2-chloropyridine (0.10 g, 0.48 mmol),Pyridine (0.057g, 0.72mmol) was dissolved in dichloromethane (0.77mL) to prepare reaction solution 1, and phenylsulfonyl chloride (0.10g, 0.58mmol) was used to prepare reaction solution 2. The flow rate (0.4mL / min) set by the intelligent numerical control sampler was simultaneously introduced into the first three-way mixer (ambient temperature 0 C) through a 500 mum inner diameter picker tube and mixed, and then flowed out under its own pressure and entered In a temperature-controlled (25 C) picker tube with an inner diameter of 500 mum, the sulfonamidation reaction is completed under the condition of a set residence time t1 (1min), and then the post-pressure valve is used to obtain a first effluent;

The chemical industry reduces the impact on the environment during synthesis 588729-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Fudan University; Zhuhai Fudan Chuangxin Institute; Ling Yun; Zhou Yaming; Jia Yu; Deng Mingli; Liu Xiaofeng; Yang Yongtai; Chen Zhenxia; (30 pag.)CN110498798; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 15862-31-4, 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.15862-31-4, name is 3-Bromo-5-nitropyridin-2-amine, molecular formula is C5H4BrN3O2, molecular weight is 218.01, as common compound, the synthetic route is as follows.

Compound 1 (2.6 g, 12.52 mmol) and iodo benzene (2.5 g,13.77 mmol )were dissolved in Toluene( 25 m) and the solution was degassed with argon. Palladium acetate (0.28 g, 6.26 mmol ) ,xanthaphos (0.545 g, 1.252 mmol) , sodium tertiary butaoxide(l .65 g, 18.78 mmol )were added. The reaction was heated at reflux under argon for 2h.The solvent was removed in vacuum and crude mass was purified by column chromatography by eluting with 20percent ethyl acetate in pet ether to get desired compound 2 ( 1 g )

Statistics shows that 15862-31-4 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-5-nitropyridin-2-amine.

Reference:
Patent; VITAS PHARMA RESEARCH PRIVATE LIMITED; RANGARAJAN, Radha; KUMAR, Rajinder; PRABHAKAR, B V; CHANDRASEKHAR, P; MALLIKARJUNA, P; BANERJEE, Ankita; WO2013/42035; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 56026-36-9, 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. 56026-36-9, name is Methyl 6-(hydroxymethyl)nicotinate. A new synthetic method of this compound is introduced below.

To a methanol (16 mL)-acetic acid (20 mL) solution of methyl 6-hydroxymethylnicotinate (1.16 g, 6.94 mmol), 10% palladium/carbon (580 mg) was added. Then, the reaction solution was stirred for 12 hours at room temperature under a 4 atmospheres (0.4 MPa)-hydrogen atmosphere, the reaction solution was filtered with Celite. The solvents of the filtrate were removed under reduced pressure to give desired piperidine derivative. The product was used for the following reaction without further purification. In a 200 mL recovery flask, to an acetonitrile (46 mL) solution of the piperidine derivative obtained in the reaction described above, a 37% formalin aqueous solution (1.24 mL) and sodium triactoborohydride (3.97 g, 18.7 mmol) were added. The reaction mixture was stirred for 30 minutes at room temperature. After adding 20% potassium carbonate aqueous solution 20 mL, the product was extracted with chloroform/methanol solution (9/1, 50 mL) six times. The combined organic layer was dried with sodium sulfate, and the solvents were removed under reduced pressure. The residue was purified with aminosilica gel column chromatography (chloroform/methanol=9/1) to give crystalline methyl 6-hydroxymethyl-1-methypiperidine-3-carboxylate (1.02 g; total yield of two steps, 79%). (0449) LCMS (M+H=188)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56026-36-9, its application will become more common.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; SUMITOMO DAINIPPON PHARMA CO., LTD.; FUSANO, Akira; KOBAYASHI, Tomonori; SAITO, Yasuhiro; KANAI, Toshio; (55 pag.)US2016/221948; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem