Day: April 6, 2022

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. 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 92992-85-3

To 2-bromo-3,5-dimethylpyridine (1 g) were added 1-(tert-butoxycarbonyl)-3-aminoazetidine (1.11 g),tris(dibenzylideneacetone)dipalladium(0)(250 mg),2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (330 mg),sodium tert-butoxide (770 mg) and toluene (8 mL) and the mixture was stirred at 120c overnight. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by NH column chromatography (hexane:ethyl acetate)to give the title compound (965 mg). MS(APCI)m/z:278(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, 92992-85-3, 2-Bromo-3,5-dimethylpyridine.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); 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. 896139-85-8, name is Imidazo[1,2-a]pyridin-7-ol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 896139-85-8

To a solution of imidazo[l,2-a]pyridin-7-ol (CAS 896139-85-8; 100 mg, 0.745 mmol) in dry DMF (4 mL) are added ethyl 2-bromo-2-methyl-propanoate (CAS 600-00-0; 444 pL, 2.98 mmol) and K2CO3 (412 mg, 2.98 mmol). The mixture is stirred at 60 C for 6 h. The reaction medium is diluted with water and extracted with DCM. Organic layers are combined, dried over Na2S04, filtered and concentrated. The crude material is purified by chromatography on silica gel (eluting with a gradient of 0 to 10% MeOH in DCM) to afford Int 67.

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, 896139-85-8, Imidazo[1,2-a]pyridin-7-ol.

Reference:
Patent; GALAPAGOS NV; DESROY, Nicolas; JONCOUR, Agnes, Marie; PEIXOTO, Christophe; TEMAL-LAIB, Taoues; TIRERA, Amynata; BUCHER, Denis; AMANTINI, David; DE VOS, Steve, Irma, Joel; BRYS, Reginald, Christophe, Xavier; (396 pag.)WO2019/238424; (2019); 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. 63071-12-5, name is (6-Methoxypyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H9NO2

The compound (55 mg, 0.40 mmol) obtained in step 2) was dissolved in thionyl chloride (1 mL) and stirred at room temperature for 2 hrs. The resulting reaction mixture was filtered and distilled in a vacuum. The residue thus obtained was used in the subsequent step without purification.

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, 63071-12-5, (6-Methoxypyridin-2-yl)methanol.

Reference:
Patent; HANMI PHARM. CO., LTD.; BANG, Keuk Chan; PARK, Chang Hee; CHOI, Jae Yul; KIM, Seo Hee; HAM, Young Jin; WO2014/3483; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75073-11-9, 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 75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of concentrated hydrochloride acid (233ml_) at 0C was added 5-iodo-6-methyl-pyridin-2-ylamine (25 g, 107 mmol, 1 eq) followed by addition of pre-dissolved sodium nitrite (29.5g, 427mmol, 4eq) in water (150ml_) in drop wise manner over period of 30 minutes. Resulting reaction mixture was stirred at room temperature for 16 hours. After complete consumption of starting material, reaction mixture was cooled to 0C, and pH was adjusted to 12 by saturated aqueous sodium hydroxide solution, extracted with DCM (3x200ml_). Combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to get brown oil (20g, crude). Crude was purified by column chromatography using silica gel (100-200 mesh). Desired compound was eluted at 4% ethyl acetate in hexane to get title compound as brown oil (8g, 30%). H NMR (400 MHz, CDCI3)8: 2.69 (s, 3H), 6.88 (d, J = 8.04 Hz, 1 H), 7.95 (d, J = 8.24 Hz, 1 H). LC-MS (m/z): 254.0 (M+H).

According to the analysis of related databases, 75073-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZOETIS LLC; MENON, Sanjay; SHEEHAN, Susan M.K.; VAILLIANCOURT, Valerie A.; WO2014/39484; (2014); A1;,
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. 1452-94-4, name is Ethyl 2-chloronicotinate, the common compound, a new synthetic route is introduced below. Safety of Ethyl 2-chloronicotinate

In a 500 ml_ dry round bottom flask with reflux condenser and magnetic stirrer was placed with 2-chloro-3-ethyl nicotinate (40.0 g, 215.5 mmol) in methanol (200 ml_). CH3ONa in methanol (25%, 65 ml_, 301.7 mmol) was added slowly and the reaction mixture was refluxed for 16 hours. The reaction was cooled to room temperature, quenched by addition of a saturated aqueous NH4CI solution. The aqueous mixture was extracted with ethyl acetate. The combined organic layers were washed well with water, brine, dried over Na2SO4 and concentrated to give 35 g of 2-methoxy-3-methyl nicotinate with 97% yield. Sodium hydride (60% in oil, 9.21 g, 230.3 mmol) was added to a dry 500 ml_ round bottom flask followed by 100 ml_ DMF. 4-Methoxyacetophenone (31.45 g, 209.44 mmol) in 50 ml_ dry DMF was added drop-wise at 00C over 30 min. The reaction mixture was stirred for 1 h at room temperature. 2-Methoxynicotinic acid methyl ester (35 g, 209.44 mmol) was dissolved in 50 ml_ dry DMF and added EPO slowly, keeping the temperature at O0C. The mixture was stirred for 16 h at room temperature, then quenched by addition of a saturated aqueous NH4CI solution and diluted with water. The solid was filtered off, washed with water and dried to give 56.7 g diketo product in 95% yield.; A solution of ethyl 2-chloronicotinitate (6.0 g, 0.0323 mol) in anhydrous methanol (10 ml_) at room temperature was added sodium methoxide (10 ml_, 25% in methanol). The reaction mixture was stirred for half hour then heated to reflux for one hour. The mixture was poured into water and extracted with ethyl acetate and the organic layer was washed with water until neutral, dried over sodium sulfate, and concentrated to give methyl 2-methoxynicotinitate (5.2 g, 96.3%).; In a 500 mL dry round bottom flask with reflux condenser and magnetic stirrer was placed with 2-chloro-3-ethyl nicotinate (40.0 g, 215.5 mmol) in methanol (200 mL), and sodium methoxide (65 mL, 301.7 mmol, 25% in methanol) was added slowly and the reaction mixture was refluxed for 16 hours. The reaction mixture was cooled to room temperature and the reaction was quenched by addition of saturated aqueous NH4CI solution, followed by extraction with ethyl acetate. The combined organic layers were washed well with water, brine, dried over Na2SO4 and concentrated to give 2-methoxy-3-methyl nicotinate (35 g, 97%). To a dry 500 mL round bottom flask was added NaH (9.21 g 230.3 mmol, 60% in mineral oil) in DMF (100 mL). 4-Methoxyacetophenone (31.45 g, 209.44 mmol) in dry DMF (50 mL) was added dropwise at 00C over 30 min. The reaction mixture was stirred for 1 h at room temperature. Then 2-methoxynicotinic acid methyl ester (35 g, 209.44 mmol) dissolved in dry DMF (50 mL) was added slowly on cooling. The mixture was stirred for 16 h at room temperature. The reaction was quenched by addition of saturated NH4CI solution and diluted with water. The solid was filtered off, washed with water and dried to give the diketo product (56.7 g, 95 %). Polyphosphoric acid (8.0 g) was heated at 900C and the diketo compound (1.0 g, 3.50 mmol) was added slowly and heated at 900C for 1 hour. The reaction mixture was cooled to room temperature and diluted with water. The solid was isolated by filtration, washed with water and dried to give 2- (4-methoxyphenyl)-4H-pyrano[2,3-b]pyridine-4-one (570 mg, 64%). MS (ES) m/z: 254.89 (M+1), 253.90 (M); MP 269-2700C.; In a 250 mL dry round bottom flask with a reflux condenser and magnetic stirrer was placed with 2-chloro-3-ethyl nicotinate (12.0 g, 64.7 mmol) in dry methanol (200 mL), and CH3ONa (21 mL, 97.0 mmol, 25% in methanol) were added slowly and the reaction mixture was refluxed for 16 hour. The reaction mixture was cooled to room temperature and quenched by addition of a saturated aqueous NH4CI solution and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give 2-methoxy-3-methyl nicotinate (10.0 g, 93%). In a dry 500 mL round bottom flask NaH (549 mg, 13.7 mmol, 60% in mineral oil) was added in DMF (10 mL). Acetophenone (1.5 g, 12.5 mmol) in dry DMF (10 mL) was added drop-wise at O0C in 30 min. The reaction mixture was stirred for 1 h at room temperature. 2- Methoxy-3-m ethyl nicotinate (2.08 g, 12.5 mmol) dissolved into dry DMF (10 mL) was added slowly on cooling. After addition the mixture was stirred for 16 h at EPO room temperature. The reaction mixture was quenched by addition of a saturated aqueous NH4CI solution and diluted with water. The solid was filtered off, washed with water and dried to give the diketo product (2.94 g, 92%). Poly phosphoric acid (15.0 g) was heated at 9O0C and the diketo compound (1.5 g, 3.50 mmol) was added slowly and heated at 9O0C for 1 hours. The reaction mixture was cooled to room temperature and diluted with water. The solid was separated by filtration, washed with water and dried to give pure 2-phenyl-4H-pyrano[2,3- b]pyridin-4-one (655 mg…

The synthetic route of 1452-94-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); 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. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid. A new synthetic method of this compound is introduced below., Formula: C6H3ClN2O4

Methyl 6-chloro-5-nitronicotinate was purchased from Sigma Aldrich or synthesized as follows. Toa solution of 6-chloro-5-nitronicotinic acid (Ark Pharm, Inc., 2.5 g, 12.3 mmol) in dry DMF (30mL) were added K2CO3 (2.5 g, 18.5 mmol) and iodomethane (8.76 g, 61.7 mmol). The solution wasstirred at room temperature for 24 h, then poured onto ice, and extracted with EtOAc (100 mL × 3).The organic layer was washed with H2O (100 mL × 2) and brine (100 mL), and dried over MgSO4.The solvent was evaporated under reduced pressure and the residue was purified by flash columnchromatography (EtOAc/n-hexane = 1/2) to afford 10 (2.4 g, 92%) as a yellow solid.

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, 7477-10-3, 6-Chloro-5-nitronicotinic acid.

Reference:
Article; Takamura, Yuta; Takahashi, Manami; Nishii, Midori; Shibahara, Osamu; Watanabe, Masaki; Fujihara, Michiko; Kakuta, Hiroki; Bioorganic and Medicinal Chemistry Letters; vol. 29; 15; (2019); p. 1891 – 1894;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 716362-10-6, 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 716362-10-6 as follows.

6-Chloro-4-methoxynicotinic acid (18) was prepared according to Ehara et al., ACS Med. Chem. Lett. 2014, 5, 787-792. To a suspension of this compound (3.87 g, 9.97 mmol) in oxalyl chloride (25 mL, 37 g, 291.5 mmol) was added DMF (0.8 mL) followed by anhydrous CH2C12(10 mL) and the reaction mixture was stirred 2 h at 60 C. Afterwards the reaction mixture was concentrated using the argon flow and the residue was dried under reduced pressure affording the respective chloroanhydride (4.0 g, 100% crude) which was immediately used for the next step.To a solution of this compound in hot EtOAc (100 mL) was added 2,3,5,6-tetrafluorophenol (2.92 g, 19.35 mmol; vigorous gas evolution was observed). Thereafter, the mixture was cooled to ambient temperature, Et3N (2.68 mL, 1.96 g, 19.35 mmol) was added dropwise and the resulting suspension was stirred for 1 h. Afterwards, the reaction mixture was washed with H20 (3 X20 mL), brine (2×20 mL), dried and concentrated under reduced pressure. The residue was taken up in CH2Cl2(70 mL), the suspension was filtered, the filter cake was washed with CH2Cl2(50 mL). The collected dichloromethane fraction was concentrated under reduced pressure. The residue was recrystallized from hexane affording 14 (2.6 g, 44%) as a colorless solid. The mother liquor was concentrated by reduced pressure and the residue was purified by column chromatography (CH2Cl2:hexane=8:2.5) giving the second crop of 14 (0.8 g, total 58%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,716362-10-6, its application will become more common.

Reference:
Patent; UNIVERSITAeT ZU KOeLN; NEUMAIER, Bernd; ZLATOPOLSKIY, Boris; KRAPF, Philipp; RICHARZ, Raphael; DRZEZGA, Alexander; (49 pag.)WO2019/175405; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1374655-69-2, 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. 1374655-69-2, name is 3-Bromo-4-ethyl-5-fluoropyridine, molecular formula is C7H7BrFN, 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.

A reaction vessel containing a mixture of 3-bromo-4-ethyl-5-fluoropyridine (0.25 g, 0.0012 mol), 4,4,4*,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (0.96 g, 0.0036 mol), and potassium acetate (0.36 g, 0.0036 mol) in 1,4-dioxane (15 mL) was purged with argon for 10 min. Next [l,l-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (0.09 g, 0.00012 mol) was added and heated at 100 C for 18 h. The reaction mixture was cooled to room temperature filtered through a bed of CELITE and the bed was washed with ethyl acetate. The filtrate was concentrated under reduced pressure to afford the crude product 4-ethyl-3-fluoro-5-(4,4,5,5tetramethyl-l ,3,2-dioxaborolan-2-yl)pyridine. MS (M+l): 252.1.

According to the analysis of related databases, 1374655-69-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, D. Jonathan; CAI, Jaiqiang; CARSWELL, Emma; COOKE, Andrew; HOYT, Scott, B.; LONDON, Clare; MACLEAN, John; PARK, Min, K.; RATCLIFFE, Paul; XIONG, Yusheng; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2013/43521; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 119248-43-0, Adding some certain compound to certain chemical reactions, such as: 119248-43-0, name is 1H-Pyrrolo[3,2-c]pyridine-3-carboxylic acid,molecular formula is C8H6N2O2, 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 119248-43-0.

Example 218 (S)-(2,7-Dimethyl-3-(3,4,5-trifluorophenyl)-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl)(1H-pyrrolo[3,2-c]pyridin-3-yl)methanone The title compound was prepared in a manner analogous to Example 288, using 1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid instead of 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid. MS (ESI): mass calcd. for C22H18F3N5O, 425.1; m/z found, 426.1 [M+H]+. 1H NMR (500 MHz, Methanol-d4) delta 8.98 (s, 1H), 8.24 (d, J=5.9 Hz, 1H), 7.82 (s, 1H), 7.52 (dd, J=5.8, 1.1 Hz, 1H), 7.35-7.27 (m, 2H), 5.66 (s, 1H), 4.52 (s, 1H), 3.82 (s, 3H), 3.50-3.36 (m, 1H), 2.94-2.84 (m, 1H), 2.60-2.50 (m, 1H), 1.65-1.60 (m, 3H).

According to the analysis of related databases, 119248-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Chen, Gang; Huang, Chaofeng; Laforteza, Brian Ngo; Ravula, Suchitra; Southgate, Emma Helen; Zhang, Wei; US2020/102303; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2510-23-8 ,Some common heterocyclic compound, 2510-23-8, molecular formula is C7H5N, 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 D-l 3-ethyne pyridine (8.0 g, 77.6 mmol) in THF (ISOmL) at -78 C, n-BuLi (1,6 M in hexanes, 54 mL, 85,3 mmol) was added dropwise (keeping the reaction temperature below -60 C), It was stirred at this temperature for another 2 hrs and warmed up to OC. It was cooled to -30 C again and a fresh chopped dry ice was added. It was stirred and allowed to warm up to 0 C and 20 mL 4.ON NaOH was added. Organic layer was separated, Aqueous layer was acidified to ph <1, Solid was filtered to yield the final product. Yield: 6.0 g 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. 2510-23-8, 3-Ethynylpyridine, other downstream synthetic routes, hurry up and to see. Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2008/14311; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem