Tag: M.W:200-300

Reference of 1083169-00-9, 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 1083169-00-9, name is 4-Bromo-2-methoxy-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of intermediate 6c (0.1M solution in THF, 66 mL,6.6 mmol) was added to a solution of 4-bromo-2-methoxy-6-methylpyridine (CAS: 1083169-00-9; 1.21 g, 6.00 mmol) and Pd(/-Bu3P)2 (140 mg, 0.27 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was treated with NH4Cl (sat., aq.) and extracted with EtOAc. The organic layer was dried (Na2S04), filtered and the solvent was evaporated in vacuo. The crude mixture was purified by flash column chromatography (S1O2, (0434) EtOAc in heptane, gradient from 100:0 to 80:20) to afford intermediate 31 (1 g, 54%).

According to the analysis of related databases, 1083169-00-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; TRESADERN, Gary John; CONDE-CEIDE, Susana; (212 pag.)WO2019/243528; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 624-28-2, Adding some certain compound to certain chemical reactions, such as: 624-28-2, name is 2,5-Dibromopyridine,molecular formula is C5H3Br2N, 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 624-28-2.

To a solution of phenol (1.97 g, 20.9 mmol) in N,N-dimethylformamide (100 mL) was added sodium hydride (1.00 g, 20.9 mmol) at 0 C., which was stirred for 5 minutes at 0 C. 2,5-Dibromopyridine (4.50 g, 19.0 mmol) was then added to this reaction solution at 0 C., and stirred for 40 minutes at room temperature. The reaction solution was then stirred for further 3 hours at 120 C. After allowing to room temperature, the reaction solution was partitioned into water and ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=6:1) to obtain the title compound (3.85 g, 81%). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 7.02 (1H, dd, J=0.55, 8.8 Hz), 7.11-7.14 (2H, m), 7.19-7.23 (1H, m), 7.38-7.43 (2H, m), 8.04 (1H, dd, J=2.6, 8.8 Hz), 8.25 (1H, dd, J=0.55, 2.6 Hz).

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. 624-28-2, 2,5-Dibromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13959-02-9, 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. 13959-02-9, name is 3-Bromoisonicotinic acid, molecular formula is C6H4BrNO2, 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.

Reference Production Example 19A mixture of 0.69 g of 3-bromo isonicotinic acid, 0.60 g of 2-amino-4-(trifluoromethyl)phenol, 1.00 g of WSC and 6 ml of pyridine was stirred while heating at 80C for two hours. The reaction mixture was cooled to room temperature, and then concentrated. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixture solvent of ethyl acetate and hexane to give 0.29 g of 3-bromo-N-[2- hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 13959-02-9, 3-Bromoisonicotinic acid.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/40629; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 154012-15-4 , The common heterocyclic compound, 154012-15-4, name is Ethyl 4,6-dichloro-5-nitronicotinate, molecular formula is C8H6Cl2N2O4, 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 4, 6-dichloro-5-nitro-nicotinic acid ethyl ester (1.00 g, 3.77 MMOL) in CH2CI2 (10 mL) at 0 C was added Et3N (0. 58 mL, 4.15 MMOL) and (3,3- dimethylbutyl) amine (0.56 mL, 4.15 MMOL). After 30 min at RT, the reaction was diluted with CH2CI2, washed with water and dried over MGSO4. The solvent was removed in vacuo to provide the desired compound as a yellow solid (1.25 g). MS (ES+) m/z 330.2 (M+H) +.

The synthetic route of 154012-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/11700; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 885167-81-7, 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. 885167-81-7, name is 6-Bromo-5-methylnicotinaldehyde, molecular formula is C7H6BrNO, 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.

Embodiment 69 (E)-2-((6-(3-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylstyryl)-5-methy lpyridin-3-yl)methylamino)-3-hydroxypropanoic acid 69 Synthetic route Synthesis of compound 69-a Compound 15-b (850mg, 2.2mmol) and 6-bromo-5-methyl nicotine aldehyde (300mg, 1.5mmol) were dissolved in a mixed solvent of 1,4-dioxane (20mL) and water (2mL), followed by addition of [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (30mg, 0.03mmol) and sodium carbonate (397mg, 3.7mmol). After the reaction system was purged three times with nitrogen, the reaction solution was heated to 80C and stirred for 12 hours. The reaction solution was cooled to room temperature and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to give compound 69-a as a yellow solid (220mg, yield 40%). LC-MS (ESI): m/z = 372 [M+H]+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 885167-81-7, 6-Bromo-5-methylnicotinaldehyde.

Reference:
Patent; Guangzhou Maxinovel Pharmaceuticals Co., Ltd.; WANG, Yuguang; XU, Zusheng; WU, Tianzhi; HE, Min; ZHANG, Nong; (113 pag.)EP3483142; (2019); 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.139042-59-4, name is 5-Acetyl-2-bromopyridine, molecular formula is C7H6BrNO, molecular weight is 200.03, as common compound, the synthetic route is as follows.COA of Formula: C7H6BrNO

In a 50 mL round-bottomed flask under nitrogen, sodium borohydride (0.390 g, 10.31 mmol) was added portionwise on 5 min to a solution of 5-acetyl-2-bromopyridine (0.515 g, 2.57 mmol) in 2-propanol (10 mL) and water (4 mL) and the mixture was stirred at room temperature for 30 min. The mixture was then concentrated in vacuo and water was added to the concentrate. The mixture was extracted with ethyl acetate (x3) and the combined organic extract was dried over anhydrous Na2SO4 and concentrated. The obtained residue was purified on the ISCO using a 25g SILICYCLE column (elution with hexanes-EtOAc) to give the title material (0.470 g, 90%) as colorless oil. LC (Method B): 1.233 min. LCMS (APCI): calcd for C7H9BrNO [M+H]+ m/z 201.986, found 202.0. 1H NMR (400 MHz, acetone-d6): delta ppm 8.38 (d, J= 2.7 Hz, 1H) 7.71 – 7.77 (m, 1H) 7.54 (d, J= 8.2 Hz, 1H) 4.92 (q, J= 6.7 Hz, 1H) 1.43 (d, J= 6.7 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139042-59-4, 5-Acetyl-2-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; PRIESTLEY, Eldon Scott; POSY, Shoshana L.; TREMBLAY, Francois Tremblay; MARTEL, Alain; MARINIER, Anne; WO2013/163241; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 15862-46-1, 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.15862-46-1, name is N-(5-Bromopyridin-3-yl)acetamide, molecular formula is C7H7BrN2O, molecular weight is 215.05, as common compound, the synthetic route is as follows.

Intermediate 61 : N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide To a suspension of A/-(5-bromopyridin-3-yl)acetamide (for a preparation see Intermediate 60, 563 mg, 2.62 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1 ,3,2-dioxaborolane) (1330 mg, 5.24 mmol) and potassium acetate (771 mg, 7.85 mmol) in 1 ,4-dioxane (8 mL) in a microwave vial, was added PdC idppf) (192 mg, 0.262 mmol). The vial was sealed and the mixture was heated in a microwave at 100C for 1 h. The mixture was dissolved in ethyl acetate and filtered through a Celite cartridge (10 g). The solvent was evaporated under reduced pressure to give A/-(5-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)pyridin-3-yl)acetamide as a brown oil (1.77 g, 258 %). This crude material was used in the next step without further purification: 100 % conversion assumed therefore maximum purity of crude material is 39 %. LCMS (2 min, High pH): Rt = 0.47 min, MH+ 263

The chemical industry reduces the impact on the environment during synthesis 15862-46-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 118175-10-3, 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 118175-10-3 as follows.

(Reference Example 4) 2-Hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine (5.0 g (23.7 mmol)) was dissolved in dichloromethane (40 ml), and thionyl chloride (4.23 g (35.6 mmol)) was added dropwise thereto so that the temperature did not exceed 25C. Following stirring at room temperature, disappearance of the raw materials was confirmed by TLC, and 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine (6.23 g) was obtained by concentrating under a reduced pressure (yield: 99.0%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,118175-10-3, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1775292; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 148760-75-2, 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 148760-75-2, name is tert-Butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70 C. for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00%).

According to the analysis of related databases, 148760-75-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); 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. 910543-72-5, name is 3-Amino-5-bromo-1-methylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H7BrN2O

To a solution of (6-Chloro-pyridin-3-yl)-(4-methyl-piperazin-l-yl)-methanone (2.0Og, 7.46 mmol) in 10 mL dimethylformamide was added 3-Amino-5-bromo-l -methyl- lH-pyridin-2-one (1.8Og, 8.95mmol) and sodium hydiride (537mg, 22.4mmol). After stirring for 18 hours, this was quenched with water. This was extracted with ethylacetate. The ethylacetate layer was dired over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 0 to 5% methanol/DCM) to yield 5-Bromo-l-methyl-3-[5-(4-methyl- piperazine-l-carbonyl)-pyridin-2-ylamino]-lH-pyridin-2-one (900mg, 1.94mmol). MS (ESI) 406.0 (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, 910543-72-5, 3-Amino-5-bromo-1-methylpyridin-2(1H)-one.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/98144; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem