Day: November 27, 2020

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. 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. 571188-59-5

900 mg of Compound 5 was dissolved in 10 mL of toluene solution. Add 4 mL of 1 mol/L LiHMDS at 0~10 CA solution of tetrahydrofuran was stirred for 1 h. Add 450 mg of compound 1 in toluene at 0~10 C and slowly return to room temperature.2.5h. After the end of the HPLC monitoring reaction, the reaction was quenched with 9 mL of saturated ammonium chloride, and the organic phase was separated, using anhydrous sulfuric acid.The sodium was dried, and the filtrate was collected by filtration.86%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Pengxu Pharmaceutical Technology Co., Ltd.; Li Pixu; Wang Peng; Wei Qiang; (7 pag.)CN109553621; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

19524-06-2, Adding a certain compound to certain chemical reactions, such as: 19524-06-2, 4-Bromopyridine hydrochloride, 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, 19524-06-2, blongs to pyridine-derivatives compound.

To a solution of 4-bromopyridine hydrochloride (8.9 g, 45.77 mmol) in dioxane (100 mL) and H20 (12.5 mL) was added cyclopropylboronic acid (5.8 g, 68.1 mmol), Pd(dppf)Cl2 (2.0 g, 2.75 mmol) and potassium phosphate (27.9 g, 131.8 mmol) under N2. The mixture was stirred at 90 C for 16 h. Water (100 mL) was added, filtered and the residue was extracted with EtOAc (100 mLx3), dried over Na2S04, filtered and concentrated in vacuum. To the residue was added HCl (5 mol/L, 50 mL), extracted with DCM (50 mL x3), the aqueous layer was basified with NaOH (5 mol/L, 100 mL) and extracted with DCM (50 mL x4), dried over Na2S04, filtered and concentrated in vacuum to afford 4-cyclopropylpyridine (4.1 g, 27.0 mmol, 59 % yield) as a black oil. MS (ES+) C8H9N requires: 119, found 120 [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,19524-06-2, its application will become more common.

Reference:
Patent; TESARO, INC.; LEWIS, Richard T.; JONES, Philip; PETROCCHI, Alessia; REYNA, Naphtali; HAMILTON, Matthew; CROSS, Jason; TREMBLAY, Martin; LEONARD, Paul Graham; (216 pag.)WO2018/136887; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

109-04-6 ,Some common heterocyclic compound, 109-04-6, molecular formula is C5H4BrN, 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.

REFERENCE EXAMPLE 31; 2-(3-Aminophenyl)pyridine; To a suspension of 2-bromopyridine (0.5 g, 3.2 mmol), 3-aminophenylboronic acid (0.49 g, 3.2 mmol), anhydrous K2CO3 (0.87 g, 6.3 mmol) and Pd(PPh3J4 (0.36 g, 0.32 mmol) in 1 ,2-dimethoxyethane (50 mL) under argon, water (0.66 mL) was added. The mixture was heated under argon at 80 C overnight. It was allowed to cool and water and EtOAc were added. The phases were separated and the aqueous phase was reextracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.22 g of the title compound (yield: 42%). LC-MS (method 1): tR = 1.46 min; m/z = 171.2 [M+H]+.

According to the analysis of related databases, 109-04-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; J. URIACH Y COMPANIA S.A.; WO2007/339; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

462-08-8, 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. 462-08-8, name is Pyridin-3-amine, the common compound, a new synthetic route is introduced below.

Example 28 Manufacturing t-butyl pyridin-3-ylcarbamate Into a solution obtained by dissolving 100.0 g (1.06 mol) of 3-aminopyridine in a mixed solvent of 300 ml of 2-propanol and 100 mL of water, a mixed solution of 266.7 g (1.22 mol) of di-t-butyl dicarbonate and 100 mL of 2-propanol was added dropwise over three hours. The inner temperature of the mixture during the dropwise addition was maintained to be 5 to 20C. After the dropwise addition was finished, the obtained mixture was stirred at room temperature for 3 hours, and the resultant was subjected to a concentration process under reduced pressure. To the concentration residue, 200 mL of water was added. After the resultant was further subjected to a concentration process, 200 mL of water was added to the concentration residue, and the deposited crystals were filtered. The obtained crystals were washed with 200 ml of water to obtain 234.2 g of hydrous crystals of t-butyl pyridin-3-ylcarbamate. The hydrous crystals were analyzed by gas chromatography with a result that the content of t-butyl pyridin-3-ylcarbamate was 79.5 wt%, with a yield of 90.2%.

Statistics shows that 462-08-8 is playing an increasingly important role. we look forward to future research findings about Pyridin-3-amine.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2269986; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 609-71-2 as follows., 609-71-2

A stirred solution of substituted anilines (1.0 mmol) in CH2Cl2 (5 mL) was treated with equimolar quantities of substituted nicotinic acids, using EDC.HCl (0.216 g, 1.2 mmol) as condensing agent. The mixture was refluxed for 8-10 h. Flash chromatography (MeOH/CH3Cl, 1:10) afforded the corresponding compound as white powder.

The chemical industry reduces the impact on the environment during synthesis 609-71-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Shi, Lei; Li, Zi-Lin; Yang, Ying; Zhu, Zhen-Wei; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 121 – 124;,
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 1121-60-4, name is Picolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. 1121-60-4

The 2-pyridine benzaldehyde (10.7g, 0.1mol),Malonic acid (25.5g, 0.25mol) was added to a 100ml round bottom flask,Add 30ml of pyridine as a solvent and stir it magnetically. After all of it is dissolved,Inject 1.6g piperidine into the system, warm the oil bath to 65 C, and react for 3h.Follow the reaction by thin layer chromatography. After the reaction is complete, cool the reaction solution to 0-5 C .Poured into a mixture of ice and water containing concentrated hydrochloric acid (12mol / l, 50ml), a large amount of white solid was precipitated and filtered with suction to obtain the desired 2-pyridineacrylic acid in a molar yield of 78%.

Statistics shows that 1121-60-4 is playing an increasingly important role. we look forward to future research findings about Picolinaldehyde.

Reference:
Patent; Changzhou Chuanyou Environmental Protection Technology Co., Ltd.; Ni Jun; (4 pag.)CN110746346; (2020); A;,
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 5470-70-2, name is Methyl 6-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows. 5470-70-2

In a 500 ml round-bottomed flask at room temperature under nitrogen, methyl 6-methyl-3- pyridinecarboxylate (10 g, 66.2 mmol) was dissolved in dry tetrahydrofuran (100 ml) to give a orange solution. The mixture was then cooled down to 00C and lithium aluminum hydride (36.4 ml, 72.8 mmol) was added dropwise, keeping internal temperature below 00C. At the end of addition the ice-bath was removed and the resulting solution was stirred at room temperature for 3 hours. The mixture was slowly additioned with 2.73 ml of water, 2.73 ml of NaOH 1 M and 8.2 ml of water. The resulting yellow suspension was stirred at room temperature for -30 minutes and then filtered over a Gooch funnel. The solid was washed with Et2O (3 x 100 ml). The combined organics were dried over Na2SO4, filtered and concentrated to give the title product (7.48 g) as orange oil.

Statistics shows that 5470-70-2 is playing an increasingly important role. we look forward to future research findings about Methyl 6-methylnicotinate.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/80637; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A common compound: 18368-63-3, name is 2-Chloro-6-methylpyridine,molecular formula is C6H6ClN, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 18368-63-3

A mixture of 2-chloro-6-methylpyridine 3e (1.30 g, 10.2 mmol), potassium carbonate (2.12 g, 15.3 mmol) and benzyl mercaptane (1.90 g, 15.3 mmol) in DMSO (10 mL) was stirred at 150 C for 3 h. After cooled to room temperature, H2O was added and extracted with EtOAc. The extract was washed with a solution of NaHCO3, H2O and brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (n-hexane/EtOAc = 15/1) to afford compound 4e (1.90 g, 87%) as a colorless oil: 1H-NMR (CDCl3) d 2.52 (3H, s), 4.41 (2H, s), 6.81-6.83 (1H, m), 6.93-6.95 (1H, m), 7.20-7.42 (6H, m).

With the rapid development of chemical substances, we look forward to future research findings about 18368-63-3.

Reference:
Article; Nishida, Haruyuki; Fujimori, Ikuo; Arikawa, Yasuyoshi; Hirase, Keizo; Ono, Koji; Nakai, Kazuo; Inatomi, Nobuhiro; Hori, Yasunobu; Matsukawa, Jun; Fujioka, Yasushi; Imanishi, Akio; Fukui, Hideo; Itoh, Fumio; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3447 – 3460;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

6419-36-9, 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. 6419-36-9, name is 2-(Pyridin-3-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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 3; Preparation of 3-pyridyl-1-hydroxyethylidene-1, 1-bisphosphonic acid monosodium salt in the presence of olive oil; The procedure of Example I is repeated except olive oil is used as the emulsifying agent instead of sunflower oil. The analysis confirmed the identity of the product and the absence of impurities. Overall yield of 27.0 % is obtained.

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. 6419-36-9, 2-(Pyridin-3-yl)acetic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EOS Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ti Caret A.S.; EP1798236; (2007); 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. 117977-21-6, name is 2-[[[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl ]methyl]thio]-1H-benzimidazole. A new synthetic method of this compound is introduced below., 117977-21-6

Example 3 Preparation of 2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridinyl]methyi]- sulfinyl]-lH-benzimidazole sodium (Rabeprazole Sodium) 2-[[ [4 -(3 -methoxy-propoxy)-3 -methyl-2-pyridinyl]methyl] -thio]-1 H benzimidazole (25 g) was suspended in 500 ml of Purified Water, Sodium hydroxide (5 g) and Pyridine (12.5 ml). To this was slowly added about 160 g of Sodium hypochlorite solution having a chlorine content of 3.2 % at 5-10 C in 2 hours. The reaction mass was maintained at 5 – 8 C for 2 hours. After completion of the reaction, excess Sodium hypochlorite was decomposed using 5% aqueous Sodium thiosulphate solution. The reaction mass was then saturated with 150 g of Sodium chloride and extracted with 250 ml of dichloromethane twice. The organic layer was then dried over anhydrous Sodium sulphate. Concentrating the organic layer under vacuum yielded a residue to which 125 ml of Ethyl acetate was added and heated to 45 – 50 C for dissolution. This solution was slowly added to 500 ml of n-Heptane under stirring and stirred for 2 hours. EPO The solids were filtered under nitrogen atmosphere, washed with n-Heptane and dried in an oven at 45-50 C to give 20 g of Rabeprazole sodium.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117977-21-6, 2-[[[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl ]methyl]thio]-1H-benzimidazole, and friends who are interested can also refer to it.

Reference:
Patent; CIPLA LIMITED; PATHI, Srinivas, Laxminarayan; KANKAN, Rajendra, Narayanrao; RAO, Dharmaraj, Ramachandra; WO2006/117802; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem