Tag: M.W:100-200

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

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

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

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

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

133627-45-9, Adding a certain compound to certain chemical reactions, such as: 133627-45-9, 2-Chloro-4-methylpyridin-3-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, 133627-45-9, blongs to pyridine-derivatives compound.

Preparation process: 15 ml of acetone and 25 ml of acetic acid are added to a solution of 8 g of 2-chloro-3-amino-4-methylpyridine in 20 ml of dichloromethane.Add 6 ml of borane dimethyl sulfide solution at 0 C.It was then stirred at room temperature (r.t.) overnight.After the reaction was completed, a 25 wt% aqueous ammonia solution was added to adjust the pH to 8.After adding 50 ml of water, it was extracted three times with dichloromethane.The organic phase was collected and dried over anhydrous sodium sulfate,The crude product of product 1-3 was spin-dried and used directly in the next step (yellow oil).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,133627-45-9, its application will become more common.

Reference:
Patent; Nanjing Jianuolin Optoelectric Technology Co., Ltd.; Hang Xiaochun; Yin Junli; Liu Ruqing; (57 pag.)CN110615787; (2019); A;,
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. 38875-53-5, name is 5-Bromo-2,3-diaminopyridine. This compound has unique chemical properties. The synthetic route is as follows. 38875-53-5

General procedure: 136 (360mg, 2.92mmol) and disuccinimido carbonate (749mg, 2.92mmol) were dissolved in chloroform (5mL) and heated at reflux for 48h under N2. The reaction was then concentrated, and the residue dissolved in a 1:3 mixture of CyHex/EtOAc (200mL) and heated to reflux for 10min. The reaction was then cooled and the precipitate filtered and dried to obtain 145 as a solid (210mg, 48%).

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, 38875-53-5, 5-Bromo-2,3-diaminopyridine.

Reference:
Article; Blackmore, Timothy R.; Jacobson, Jonathan; Jarman, Kate E.; Lewin, Sharon R.; Nguyen, William; Purcell, Damian F.; Sabroux, Helene Jousset; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 195; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

698-51-1, 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. 698-51-1, name is 3,5-Dichloro-2,6-difluoropyridine, molecular formula is C5HCl2F2N, 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 4 A reaction vessel was charged with 45.0 g (0.5 mole) of methyl glycolate and 13.3 g (0.125 mole) of anhydrous sodium carbonate. The resulting mixture was heated to 110 C. for 10 minutes, with methanol being allowed to strip off as it condensed. Thereafter 18.4 g (0.1 mole) of 3,5-dichloro-2,6-difluoropyridine was added to the reaction vessel, and the mixture was stirred at 110 C. for 1 hour. The stripped methanol (approximately 4 ml) and 64 g of fresh methanol were added to the slurry, which was refluxed for 1 hour at 70 C. and filtered. The filtrate was cooled to approximately 10 C. to give fine white crystals which were filtered, washed with cold methanol, and air dried. The resulting solid was further purified by being dissolved in warm perchloroethylene, filtered and cooled to give a solid precipitate. Filtration and air-drying gave 12.0 of a solid product which was identified by gas-liquid chromatography and nuclear magnetic resonance to be the desired product, 3,5-dichloro-6-fluoro-2-pyridinyloxyacetate, m.p. 72.2-73.0 C., of approximately 99% purity. The filtrates from the previous isolations were combined and concentrated by vacuum stripping. The residue was extracted twice with hot methylene chloride, and the filtered extracts were concentrated to remove the solvent, leaving 11.0 g of product which solidified on cooling.

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. 698-51-1, 3,5-Dichloro-2,6-difluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Dow Chemical Company; US4127582; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.109-04-6

To a -40 C. solution of 2.5 M n-BuLi (18 mL) in THF (300 mL) is added 2-bromopyridine (5.0 g, 32 mmol) over 15 min. The reaction is stirred for 1 h at -40 C., and then treated with 2-Amino-5-bromo-benzoic acid (6.9 g, 32 mmol) in THF (300 mL). The reaction is warmed to 0 C. and stirred for 2 h then quenched with TMSCl (3.4 g, 32 mmol). The reaction is stirred at room temperature for 30 min then cooled to 0 C. and quenched with 3M HCl (20 mL). The aqueous layer is separated and the organic layer is extracted with 3M HCl. The organic layer is basified with solid NaOH, the resulting mixture is extracted with EtOAc, and the organic layer is dried over Na2SO4, filtered and concentrated. The residue is purified by column chromatography on silica gel to give the desired product as a yellow solid. Yield: 5.50 g (62.7%) HPLC-MS: M+H=277/279; tRet=3.16 min; AM6

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 109-04-6.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; SMETHURST, Christian; ENGELHARDT, Harald; GIANNI, Davide; REISER, Ulrich; US2014/296230; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A common compound: 5470-70-2, name is Methyl 6-methylnicotinate,molecular formula is C8H9NO2, 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., 5470-70-2

[Step 1] Synthesis of methyl 6-bromomethylnicotinate methyl 6-methylnicotinate (1 g) was dissolved in carbon tetrachloride (100 ml), and N-bromosuccinimide (1.3 g) was added. The mixture was heated under reflux in an argon atmosphere for 8 hours, and allowed to cool. The precipitated crystals were removed by filtration, and the solvent was evaporated from the filtrate under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/methylene chloride=1:3) to obtain the title compound (540 mg, 35%). m.p.: 75.2-76.3 C. IR spectrum (KBr tab.) nucm-1: 1728, 1713, 1595, 1435, 1286, 1124, 1103. NMR spectrum (*DMSO-d6) delta ppm: 9.05 (1H, s), 8.34-8.30 (1H, m), 7.71 (1H, d, J=7.9 Hz), 4.77 (2H, s), 3.89 (3H, s).

With the rapid development of chemical substances, we look forward to future research findings about 5470-70-2.

Reference:
Patent; Mochida Pharmaceutical Co., Ltd.; US6018046; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem