Tag: M.W:200-300

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.848366-28-9, name is 5-Bromo-3-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-3-chloro-2-methoxypyridine

To a glass vial was added 4-methoxy-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (WO 2008/130481 , p 47) (0.273 g, 1.65 mmol), 5-bromo-3-chloro-2-methoxypyridine (0.368 g, 1.65 mmol), sodium ferf-butoxide (318 mg, 3.31 mmol), diacetoxypalladium (0.037 g, 0.17 mmol), X-Phos (0.079 g, 0.17 mmol) and anhydrous toluene / ferf-butanol, 5 /1 (6 mL). The vial was flushed with a stream of argon for 15 sec and capped. The mixture was heated with stirring for 2h at 1 10C then allowed to cool to room temperature and stirred at rt for 5 days. Diluted with CH2CI2 (10 mL) and water (2 mL), filtered through a celite pad. The organic phase was separated by filtering through a phase separation tube and concentrated in vacuo. Purified by flash chromatography on silica gel with heptane / EtOAc 100 / 0 to 0/ 100 to give 6-(5-chloro-6-methoxy-pyridin-3-yl)-4-methoxy-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine as a yellow solid (95 mg, 19% yield) LCMS: [M+H]+=307.0 / 308.9, Rt (3)= 1.62 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,848366-28-9, 5-Bromo-3-chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53937-02-3 , The common heterocyclic compound, 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone, molecular formula is C12H11NO2, 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.

A suspension of 4-(benzyloxy)pyridin-2(lH)-one (426 mg, 2.12 mmol), tert-hvXy 7-bromo-9-tosyl-3,4-dihydro-l/f-pyrido[3,4-delta]indole-2(9H)-carboxylate (1.28 g, 2.54 mmol), CuI (484 mg, 2.54 mmol), 8-hydroxyquinoline (369 mg, 2.54 mmol) and Cs2COs (760 mg, 2.33 mmol) in DMSO (10 mL) was degassed under reduced pressure for 45 min. Attorney’s Docket 2882.023BThe suspension was put under Ar and heated at 135 0C with stirring for 1.5 h. The suspension was cooled, 4:1 CH2C12/(9:1 MeOH/NH4OH) (50 niL) was added and the resulting suspension was stirred at 25 0C for 10 min. The suspension was passed through a plug of silica gel and the filtrate was washed with brine. The solution was dried over Na2SO4 and concentrated under reduced pressure to afford an amorphous solid. Flash chromatography (silica gel, (1 :1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH) 100:0 to 0:100) yielded the title compound (715 mg, 54%) as an off-white solid: 1H NMR (300 MHz, CDCl3) delta 8.18 (br s, IH), 7.82-7.73 (m, 2H), 7.48-7.35 (m, 6H), 7.33-7.23 (m, 4H), 6.12-5.97 (m, 2H) 5.07 (s, 2H), 4.90 (br s, 2H), 3.72-3.64 (m, 2H), 2.73-2.63 (m, 2H), 2.34 (s, 3H), 1.51 (s, 9H).

The synthetic route of 53937-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); 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. 134896-35-8, name is 3-Nitro-2-phenylpyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C11H8N2O2

Step 2 cis-2-Phenyl-3-aminopiperidine A solution of 30 g (0.15 mol) of 2-phenyl-3-nitropyridine in 190 mL of methanol was hydrogenated using 5 g of platinum oxide with an initial pressure of 45 psi hydrogen. After 2 h, 50 mL of conc HCl was added, the vessel repressurized to 45 psi, and the reduction continued for an additional 6.25 h. The reaction was diluted with water (100 mL) and filtered. Three reactions were combined at this point and the combined cake washed with methanol (200 mL), water (100 mL), methanol (200 mL), water (100 mL), and methanol (200 mL). The filtrate was concentrated, the residue treated with 500 mL of 5N NaOH and extracted with ether (3*1 L) and methylene chloride (2*1 L). The combined extracts were dried with sodium sulfate, filtered and the filtrate concentrated to afford 80.9 g of a pale yellow oil. Chromatography (5 kg Silica Gel 60, 70-230 mesh, methylene chloride/methanol/ammonium hydroxide 92.5:7.5:0.75) afforded 62 g (78% yield) of cis-2-phenyl-3-aminopiperidine as a pale yellow oil: 1H NMR (CDCl3) delta 1.35-1.55 (m, 4H), 1.65-1.98 (m, 3H), 2.75 (m, 1H), 2.95 (m, 1H), 3.17 (m, 1H), 3.8 (bs, 1H), 7.19-7.37 (m, 5H). MS (EI) m/z 176.

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, 134896-35-8, 3-Nitro-2-phenylpyridine.

Reference:
Patent; Merck & Co., Inc.; US6241964; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, the common compound, a new synthetic route is introduced below. Safety of Methyl 6-chloro-5-nitronicotinate

Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl 2-(benzylamino)acetate (6.0 g, 31.05 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one h and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30percent gradient, ethyl acetate in hexanes) to yield the title compound (3.10 g, 90percent yield) as a yellow oil. [M+H] calc’d for C18H19N3O6, 374; found, 374.

The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2010/190763; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 30766-11-1 , The common heterocyclic compound, 30766-11-1, name is 5-Bromopicolinic acid, molecular formula is C6H4BrNO2, 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 mixture of 5-bromopyridine-2-carboxylic acid (2.5 g, 12 mmol) in methylene chloride (10.0 mL) was added oxalyl chloride (1.6 mL, 18 mmol), followed by N,N-dimethylformamide (0.020 mL, 0.26 mmol). After stirred at RT for 2 h, the mixture was evaporated under reduced pressure. The residue was the acid chloride which was used directly in next step reaction.

The synthetic route of 30766-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhuo, Jincong; Qian, Ding-Quan; Yao, Wenqing; US2007/129345; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 942920-55-0, Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate, 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, Application In Synthesis of Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate, blongs to pyridine-derivatives compound. Application In Synthesis of Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

To a mixture ethyl 4-bromo-1 H-pyrrolo[2,3-b]pyridine-2-carboxylate (500 mgs, 1.86 mmol) and 2-((tetrahydro-2H-pyran-4-yl)oxy)-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzonitrile (673 mgs, 2.0 mmol) in DME (6 mL) was 2.0 M aqueous Na2CO3 (2.0 mL, 4 mmol) and Pd(PPh3)4 (107 mgs, 0.09 mmol). The reaction mixture was heated at 140 C for 1 hr. After cooling to rt, ethyl acetate (10 mL) and water (20 mL) was added and the solids were filtered and washed with water and dried to give ethyl 4-(3-cyano-4-((tetrahydro-2H-pyran-4-yl)oxy)phenyl)-1 H-pyrrolo[2,3- b]pyridine-2-carboxylate (500 mgs) LCMS-ESI+ (m/z): [M+H]+ calcd for C22H21 N3O4 as (M+H)+ 392.4 found: 392.1

The synthetic route of 942920-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; DU, Zhimin; GUERRERO, Juan, Arnaldo; KAPLAN, Joshua, Aaron; KNOX, JR., John Edward; NADUTHAMBI, Devan; PHILLIPS, Barton, W.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William, J.; ZABLOCKI, Jeff; WO2015/187684; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 93349-99-6, 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. 93349-99-6, name is Methyl 5-bromo-6-methoxynicotinate, molecular formula is C8H8BrNO3, 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.

Methyl 5-bromo-6-methoxynicotinate (1 g),Ethynyltriisopropylsilane (1.5 ml),Bis (triphenylphosphine) dichloropalladium (280 mg),Copper (I) iodide (80 mg),Triethylamine (1.6 ml), And acetonitrile (15 ml)And the mixture was stirred overnight at 80 C. under a nitrogen atmosphere.The mixture was cooled to room temperature and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine,Dried over magnesium sulfate and then concentrated under reduced pressure. THF (15 ml) and 1 M tetrabutylammonium fluoride THF solution (8 ml) were added to the obtained residue, and the mixture was stirred at room temperature for 1 hour. The mixture was extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (0.55 g)

According to the analysis of related databases, 93349-99-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; MIZOJIRI, RYO; CARY, DOUGLAS ROBERT; HIRAYAMA, TAKAHARU; ITO, MASAHIRO; TANAKA, TOSHIO; IMAEDA, YASUHIRO; SASAKI, SHIGEKAZU; TAKAMI, KAZUAKI; FUKUDA, KOICHIRO; KAMAURA, MASAHIRO; MORISHITA, NAO; (133 pag.)JP2017/222626; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-82-3 , The common heterocyclic compound, 153034-82-3, name is 2-Fluoro-4-iodonicotinaldehyde, molecular formula is C6H3FINO, 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.

[00343] (2-Fluoro-4-iodopyridin-3-yl)methanol F OH. To a solution of 2-fluoro-4- iodonicotinaldehyde (3.50 g, 13.94 mmol) in absolute EtOH (56 mL) was added sodium borohydride (0.264 g, 6.97 mmol) at room temperature. The reaction was stirred at room temperature for 1 h, followed by the slow addition of 1 M aqueous hydrochloric acid. The product was extracted with CH2CI2 (repeated four times), and the organic layers were combined, dried over sodium sulfate, filtered and concentrated to dryness. The aqueous phase was basified to pH 8-10 with 2 M aqueous sodium hydroxide and extracted with diethylether (repeated four times). Then the organic layers were combined, dried over sodium sulfate, filtered, combined with the previously obtained residue and concentrated to dryness under vacuum. The residue was used without any purification in the next step. LC/MS m/z 254[M+H]+.

The synthetic route of 153034-82-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; AUDIA, James Edmund; COTE, Alexandre; GEHLING, Victor S.; HARMANGE, Jean-christophe; HEWITT, Michael C.; LEBLANC, Yves; NAVESCHUK, Christopher G.; TAYLOR, Alexander M.; VASWANI, Rishi G.; WO2012/75383; (2012); A2;,
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. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. A new synthetic method of this compound is introduced below., Product Details of 588729-99-1

Step 1. 6-Bromo-thiazolo [5,4-b] pyridin-2-yl amine:(Intermediatel) In a 50ml RB flask, 5-bromo-2-chloropyridin-3-amine (3.11 g, 15 mmol) was taken in cone. HCl (30 mL) and sonicated well to give pale brown solution. To this potassium thiocyanate (2.187 g, 22.50 mmol) was added and the resulting mixture was heated at 1000C for 6hrs .The reaction mixture was changed to pale yellow suspension after 30 minutes of reflux. The reaction mixture was evaporated in vacuo; ice-cold water was added to the residue, sonicated well and neutralized with saturated sodium carbonate under cooling condition. The precipitated solid was sonicated well, filtered and dried under high vacuum afforded the product as off-white solid (2.5gm)MS (ES+): 231 Rw C6H4BrN3S1H NMR 5(DMSO-dfi): 5.85 (bs, 2H,NH2); 7.3 (s, lH,Aro); 7.65 (s, lH,Aro).

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, 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 66572-56-3, 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. 66572-56-3, name is 2-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.

General procedure: To a solution of 3-iodo-4-methylbenzoic acid 5-1 (262mg, 1.0mmol) in dry DCM (10mL) at 0C was added oxalyl chloride (0.13mL, 1.5mmol) and 3 drops of dry DMF. The resulting reaction mixture was stirred at room temperature for 3h, and then the solvent was removed under reduced pressure. The crude product was used directly for the next step without further purification.

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 66572-56-3, 2-Bromoisonicotinic acid.

Reference:
Article; Liu, Yang; Peng, Xia; Guan, Xiaocong; Lu, Dong; Xi, Yong; Jin, Shiyu; Chen, Hui; Zeng, Limin; Ai, Jing; Geng, Meiyu; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 122 – 132;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem