Month: September 2021

Reference of 121912-29-6, 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. 121912-29-6, name is Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Step 2: Synthesis of 1-(4-pyridyl)-4-piperidinecarboxylic acid hydrochloride: 2.95 g (12.6 mmol) of ethyl 1-(4-pyridyl)-piperidine-4-carboxylate was stirred in 100 ml of dioxane. After adding 50 ml of 1 N hydrochloric acid, the obtained mixture was stirred at 95C for 20 hours. The solventwas evaporated under reduced pressure to obtain the title compound. Yield: 3.21 g (11.5 mmol) (91 %) MS (ESI, m/z) 207 (MH+) H-NMR (DMSO-d6) delta 1.54 (2H, t), 1.90 (2H, d), 2.60-2.70 (1H, m), 3.30 (2H, t), 4.10 (2H, d), 7.19 (2H, d), 8.20 (2H, d)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,121912-29-6, Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Ajinomoto Co., Inc.; EP1065200; (2001); 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. 13194-60-0, name is 3-Chloro-4-nitropyridine. A new synthetic method of this compound is introduced below., Computed Properties of C5H3ClN2O2

3-chloro-4-nitropyridine (5 g, 31.63 mmol), 3-pyridineboronic acid (3 g, 37.75 mmol) was added to a 500 ml single-necked flask.50 ml of a 2 M potassium carbonate aqueous solution was dissolved in a solvent of 50 ml of ethanol and 100 ml of toluene.Under the protection of N2, PdCl2(PPh3)2 (0.75 g, 0.98 mmol) was added. The temperature was slowly raised to 100 C, and the mixture was reacted under reflux for 24 hours.After cooling, the layers were separated, and the organic layer was evaporated, and then, with petroleum ether and ethyl acetate (1.5:1).4.5 g of a pale yellow solid were obtained in a yield of 60%.

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, 13194-60-0, 3-Chloro-4-nitropyridine.

Reference:
Patent; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Mu Guangyuan; Zhuang Shaoqing; Ye Shaofeng; (96 pag.)CN109422743; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 54189-82-1, 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. 54189-82-1, name is 6-Chloro-N-methylnicotinamide, molecular formula is C7H7ClN2O, 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.

Example 101 Preparation of N-Methyl-6-(1-oxo-2-(2-(pyrrolidin-1-yl)ethyl)-1,2,3,4-tetrahydro-isoquinolin-6-yloxy)nicotinamide hydrochloride A suspension of NaH (60% dispersion in mineral oil, 0.06 g, 5.4 mmol) in DMF at room temperature was treated dropwise over a 15 min period with a solution of 6-hydroxy-2-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroisoquinolin-1(2H)-one (0.2 g, 2.7 mmol) in DMF, stirred at room temperature for 30 min, treated with a solution of 6-chloro-n-methylnicotinamide in DMF, heated at 100 C. overnight, cooled to room temperature, diluted with water and extracted with CH2Cl2. The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by ISCO CombiFlash chromatography (silica, 0-15% methanol in methylene plus 0.5% ammonium hydroxide) to afford the free amine of the title product as a colorless oil. The oil was dissolved in ethanol, treated with ethereal HCl, stirred and filtered. The filtercake was washed with ether and dried to provide the title compound as a white solid, 30 mg (10%), mp 228-230 C.; identified by NMR and mass spectral analyses. MS (ES) m/z 395.2 [M+H]+.

According to the analysis of related databases, 54189-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2009/69300; (2009); 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. 18438-38-5, name is 2-(Methylthio)pyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

EXAMPLE 7 An aqueous solution consisting of (i) 522.7 g (1.2 mol) of a 27% sodium hypobromite aqueous solution prepared by instilling bromine into a 30% sodium hydroxide aqueous solution and (ii) 8.4 g (0.2 mol) of 95% sodium hydroxide was cooled to 0 C. The 23.8 g of 2-(methylthio)pyridine obtained in Example 6 was instilled into this aqueous solution over 3 hours while keeping the temperature at 0 to 5 C., and stirring was then carried out for 7 hours at 0 to 5 C. The reaction product, which precipitated out as crystals, was filtered, washed with water, and dried, thus obtaining 71.1 g of 2-(tribromomethylsulfonyl)pyridine (purity 99%). The yield relative to the 2-(methylthio)pyridine was 95.0%. The melting point of the 2-(tribromomethylsulfonyl)pyridine obtained was 160 to 161 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, 18438-38-5, 2-(Methylthio)pyridine.

Reference:
Patent; Sumitomo Seika Chemicals Co., Ltd.; US6420564; (2002); B1;,
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. 6311-35-9, name is 6-Bromonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromonicotinic acid

EXAMPLE 31 2-bromo-5-[(2-methylpyrrolidin-1-yl)carbonyl]pyridine The desired product was prepared by substituting 6-bromonicotinic acid for 2-methylnicotinic acid in Example 1. After workup the crude compound was purified by HPLC on C-18 column using a solvent system increasing over 50 minutes in a gradient of 5% to 100% acetonitrile/water containing 0.01% TFA to provide the desired product as the trifluoroacetate salt. MS m/e 268.9 (M+H)+; 1H NMR (DMSO-d6) delta0.86 (d, 0.75H), 1.25 (d, 2.25H), 1.48-1.63 (m, 1H), 1.66-1.80 (m, 1H), 1.81-1.97 (m, 1H), 2.00-2.13 (m, 1H), 3.27-3.37 (m, 0.5H), 3.45-3.54 (m, 1.5H), 3.88-4.00 (m, 0.25H), 4.09-4.21 (m, 0.75H), 7.72 (d, 1H), 7.87 (dd, 1H), 8.52 (d, 1H).

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, 6311-35-9, 6-Bromonicotinic acid.

Reference:
Patent; Haviv, Fortuna; Brandley, Michael F.; Henkin, Jack; US2003/195192; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 95652-77-0, 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.95652-77-0, name is Methyl 2-chloro-6-methoxynicotinate, molecular formula is C8H8ClNO3, molecular weight is 201.61, as common compound, the synthetic route is as follows.

To a reaction vial containing 7-amino-4-chloro-isoindolin-l-one (365 mg, 2.0 mmol) in dioxane (2.0 mL) was added methyl 2-chloro-6-methoxynicotinate (603 mg, 3.0 mmol), cesium carbonate (1.3 g, 4.0 mmol), copper iodide (152 mg, 80 mmol) and (S,2S)- Nl,N2-dimethylcyclohexane-l,2-diamine (227 mg, 1.6 mmol). The mixture was purged with nitrogen, then warmed to 110 C. The reaction was stirred at 110 C and monitored by LC- MS. Following completion, the reaction was allowed to cool and was then filtered through Celite and rinsed with ethyl acetate. The crude was purified by silica gel chromatography (0- 50% ethyl acetate/hexane) to give the product.

Statistics shows that 95652-77-0 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-6-methoxynicotinate.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; KRASINSKI, Antoni; LELETI, Manmohan, Reddy; MALI, Venkat; MCMAHON, Jeffrey; SINGH, Rajinder; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; (198 pag.)WO2017/87607; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1211534-25-6, 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.1211534-25-6, name is 4-Bromo-5-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.

[00266j 28F. 4-(4-(Qert-Butyldimethylsilyl)oxy)-3 -fluoropiperidin- 1 -yl)-5 -chloro-2- methoxypyridine: A mixture of 28E (194 mg, 0.830 mmol), 27B (185 mg, 0.830 mmol) and SPhos precatalyst (6.0 mg, 8.3 jimol) in THF (1.7 mL) was purged with argon and a 1 M solution of LHMDS in THF (1.0 mL, 1.0 mmol) was added. The reaction mixturewas heated to 70 C for 2 h and then cooled to rt. Sat. aq. NaHCO3 (10 mL) was added slowly to the reaction mixture. The mixture was then extracted with EtOAc (2 x 10 mL) and the combined organic extracts were washed with water (20 mL) and brine (20 mL), dried (Na2504), filtered, and concentrated. Purification by silica chromatography gave 28F (182 mg, 0.490 mmol, 58% yield). LC-MS Anal. Calc?d for C17H28C1FN2O2Si:374.16,found[M+H] 374.9.

The chemical industry reduces the impact on the environment during synthesis 1211534-25-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ELLSWORTH, Bruce, A.; JURICA, Elizabeth, A.; SHI, Jun; EWING, William, R.; YE, Xiang-Yang; WU, Ximao; ZHU, Yeheng; SUN, Chongqing; WO2014/78609; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 17288-32-3, 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 17288-32-3 as follows.

A solution of ethyl 1H-pyrrolo[3,2-b]pyridine-2-carboxylate (23 g, 0.12 mol), 2- bromoethanol (37.9 g, 0.303 mol) and triphenylphosphine (79.4 g, 0.303 mol) intetrahydrofuran was cooled to 0 °C . Diisopropyl azodicarboxylate (61.2 g, 0.303 mol) was added drop-wise over 20 minutes and the resulting mixture was warmed to 25 °C and stirred for 18 hours. After the solvent had been removed under reduced pressure, the residue was diluted with ethyl acetate (300 mL) and extracted with aqueous hydrochloric acid (1 M, 3 x 100 mL). The combined aqueous extracts were basified topH 8 – 9 using saturated aqueous sodium carbonate solution, and the resulting mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were concentrated in vacuo; silica gel chromatography (Eluent: 5:1 petroleum ether I ethyl acetate) provided the product as a white solid. Yield: 25 g, 84 mmol, 70percent. H NMR (400 MHz, CDCI3) oe 8.59 (dd, J=4.5, 1.3 Hz, 1 H), 7.81 (br d, J=8.5 Hz, 1 H), 7.50 (br s, 1 H),7.28 (dd, J=8.5, 4.5 Hz, 1H), 4.92 (t, J=6.7 Hz, 2H), 4.42 (q, J=7.2 Hz, 2H), 3.73 (t, J=6.7 Hz, 2H), 1.44 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17288-32-3, its application will become more common.

Reference:
Patent; PFIZER INC.; CHAPPIE, Thomas Allen; CHANDRASEKARAN, Ramalakshmi Yegna; HELAL, Christopher John; LACHAPELLE, Erik Alphie; PATEL, Nandini Chaturbhai; SCIABOLA, Simone; VERHOEST, Patrick Robert; WAGER, Travis T.; (202 pag.)WO2016/203347; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 88511-27-7, Adding some certain compound to certain chemical reactions, such as: 88511-27-7, name is 4-Amino-3-iodopyridine,molecular formula is C5H5IN2, 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 88511-27-7.

General procedure: a suspension of 3-iodo-4-aminopyridine (1 mmol), methyl 2-mercaptoacetate (1.5 equiv), copper (I) iodide (0.05 mmol), trans-N,N’-dimethylcyclohexane-1,2-diamine (0.1 mmol) and cesium carbonate(2 equiv) in dry 1,4-dioxane (4 mL) in a vial was degassed by bubbling N2 into the suspension for 3 min while stirring. The vial was then capped tightly. The mixture was heated at 100 C (oil bath temperature) for 15 h. After coolingto rt, filtration was carried out. The combined filtrates were concentrated on rotavap and the residue was subjected to silica gel column chromatographpurification (5% methanol in methylene chloride) furnishing 3b as a beige solid. 1H NMR (400 MHz, CD3OD) d 8.42 (s, 1H, ArH), 8.26 (s, 1H, ArH), 6.96 (d,J = 5.4 Hz, 1H, ArH), 3.40 (s, 2H, CH2). 13C NMR (400 MHz, CD3OD) d 167.4,148.4, 148.1, 146.0, 29.6.

According to the analysis of related databases, 88511-27-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Wei-Sheng; Xu, Rongsong; Dodd, Rory; Shakespeare, William C.; Tetrahedron Letters; vol. 54; 38; (2013); p. 5214 – 5216;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6937-03-7, Adding some certain compound to certain chemical reactions, such as: 6937-03-7, name is Methyl 2-aminoisonicotinate,molecular formula is C7H8N2O2, 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 6937-03-7.

To a mixture of compound 69.10 (60 g, 394.35 mmol, 1 eq) and DMAP (2.41 g,19.72 mmol, 0.05 eq) in t-BuOH (600 mL) and ACETONE (200 mL) was added Boc20(344.26 g, 1.58 mol, 362.38 mL, 4 eq) dropwise at 18C underN2. The mixture was stirred at 18 C for 15 hours. The solution was diluted with pentane (200 mL), cooled in the refrigerator for 3 hours and filtered to obtain compound 69.9 (42 g, 166.5 mmol, 42% yield) as a white solid. ?H NMR (400 MHz, DMSO-d6) & 1.38 – 1.54 (m, 9 H), 3.82-3.96 (m, 3 H),7.44 (dd, J5.07, 1.41 Hz, 1 H), 8.32 (s, 1 H), 8.42 (d, J5.14 Hz, 1 H) and 10.11 (s, 1 H) ppm.

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. 6937-03-7, Methyl 2-aminoisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CORTEXYME, INC.; LYNCH, Casey C.; KONRADI, Andrei; GALEMMO, JR., Robert A.; (218 pag.)WO2018/209132; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem