Day: March 9, 2022

Synthetic Route of 1532517-95-5, 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. 1532517-95-5, name is 5-Bromo-3-fluoro-2-nitropyridine. A new synthetic method of this compound is introduced below.

A solution of 5-bromo-3-fluoro-2-nitropyridine (400 mg, 1.81 mmol) and 2-methoxyethanamine (408 mg, 5.43 mmol) in tetrahydrofuran (10 mL) was stirred at 25 C. for 2 hours, whereupon it was diluted with ethyl acetate (100 mL) and washed with water (50 mL). The organic layer was washed with saturated aqueous sodium chloride solution (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford C18 as a yellow solid. Yield: 430 mg, 1.56 mmol, 86%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1532517-95-5, 5-Bromo-3-fluoro-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; Aspnes, Gary Erik; Bagley, Scott W.; Curto, John M.; Edmonds, David James; Flanagan, Mark E.; Futatsugi, Kentaro; Griffith, David A.; Huard, Kim; Lian, Yajing; Limberakis, Chris; Londregan, Allyn T.; Mathiowetz, Alan M.; Piotrowski, David W.; Ruggeri, Roger B.; (127 pag.)US2019/382384; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58481-17-7, 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 58481-17-7, name is Methyl 2-(hydroxymethyl)isonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-(hydroxymethyl)isonicotinate (8.36 g, 50 mmol) was dissolved in dichloromethane (150 ml_). Dess-Martin periodinane (25 g, 58.94 mmol) was added and the mixture stirred at room temperature for 2 h 30 min. Sodium sulfothioate (59.3 g, 375.00 mmol) was dissolved in satd NaHCO3 and added to the reaction mixture. The suspension was vigorously stirred at room temperature for 15 min, DCM was added and the phases were separated. The aqueous phase was extracted with DCM twice and the combined organic layers were dried over MgSO and evaporated. The residue was purified by automated flash chromatography on a Biotage KP-SIL 340g column. Gradient heptanes / EtOAc 80:20 to 65:35 over 5 CV was used as mobile phase. Methyl 2-formylisonicotinate (7 g, 85 %) was isolated as an off-white solid. 1H NMR (400 MHz, cdcl3) delta 4.00 (s, 3H), 8.09 (dd, 1 H), 8.49 (s, 1 H), 8.95 (d, 1 H), 10.15 (s, 1 H). MS m/z 165 (M+H)+

According to the analysis of related databases, 58481-17-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; CHENG, Leifeng; SCHELL, Peter; WO2012/47156; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 856851-48-4, 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 856851-48-4 as follows.

Hydrogen peroxide-urea complex (31 .04 g, 330 mmol) was added in one portion to a solution of 2-chloro-5-ethoxypyridine (26.0 g, 1 65 mmol) in dichloromethane (250 mL) at 0 00 then trifluoroaceticanhydride (62.4 g, 297 mmol, 41 .3 0 mL) was added dropwise. The mixture was stirred at 20 00 for 16 h. The reaction mixture was quenched by addition of saturated aqueous sodium thiosulfate (150 mL). The mixture was extracted with dichloromethane (200 mL x 3), then the combined organic phases were washed with saturated aqueous sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give a crude residue that was purified by chromatography (silica, petroleumether : ethyl acetate 1:0 to 1:2) to give 2-chloro-5-ethoxypyridine 1-oxide (22.0 g, 126.7 mmol, 77%) as a yellow solid. 1H NMR (400 MHz, ODd3) O 8.05 (d, J2.6 Hz, 1 H), 7.29 (d, J9.0 Hz, 1 H), 6.81 (dd, J2.6, 9.1 Hz, 1 H), 3.97 (q, J6.9 Hz, 2H), 1 .37 (t, J7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,856851-48-4, its application will become more common.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 696-42-4, 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. 696-42-4, name is 5-Fluoronicotinonitrile, molecular formula is C6H3FN2, 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.

Produced in Reference Example 33 3- (piperidin-4-yl)-lH-pyrazol-5-amine hydrochloride (0.400 g, 1.67 mmol) in dimethyl sulfoxide (4 mL) suspension of 1,8 – diazabicyclo [5.4.0] -7-undecene (0.750mL, 5.02mmol) was added, and the mixture was stirred for 10 minutes at room temperature.Then, 3,6-dichloro pyridazine (0.249 g, 1.67 mmol) and the mixture was stirred for 4 hours at 1 hour, 60 C. at room temperature.After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate.The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, under reduced pressure, and the solvent was evaporated.The obtained residue was purified by silica gel column chromatography to obtain [eluent: ethyl acetate / methanol = 95 / 5-90 / 10 (gradient) to give the title compound (71% 0.330 g, yield) It was.Instead of 3,6-dichloro-pyridazine, 5-fluoro-3-carbonitrile (0.204 g, 1.67 mmol) using, the same procedure was followed as the method described in Reference Example 34, the title compound ( 0.167g, yield: 37%) was obtained.

According to the analysis of related databases, 696-42-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo company limited; Sato, Rie; Kobayashi, Katsuhiro; Kaneko, Toshio; (188 pag.)JP2015/113323; (2015); A;,
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. 107351-82-6, name is 2-Bromo-5-phenylpyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2-Bromo-5-phenylpyridine

Reference Example 56 2-(5-Phenyl-pyridin-2-yl)-propionic acid methyl ester STR209 The desired compound was obtained from 2-bromo-5-phenylpyridine (M. G. Knize, et al., Heterocycles, 24, 1815 (1986)) by the known method described in T. Sakamoto, et al., Heterocycles, 36, 2509 (1993). 1 H-NMR (270 MHz, CDCl3) delta ppm: 1.61(d, 3H, J=7.3 Hz), 3.72(s, 3H), 4.01(q, 1H, J=7.3 Hz), 7.34-7.59(m, 6H, 7.85 (dd, 1H, J=8.2, 2.3 Hz), 8.78(d, 1H, J=2.3 Hz)

The synthetic route of 107351-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Pharmaceutical Company, Limited; US6100260; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 183208-34-6, Adding some certain compound to certain chemical reactions, such as: 183208-34-6, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one,molecular formula is C7H5BrN2O, 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 183208-34-6.

Example 44A tert-butyl (1S,2Z)-2-(5-bromo-2-oxo-1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-3-ylidene)-1-(1H-indol-3-ylmethyl)ethylcarbamate A mixture of 5-bromo-7-aza-oxindole (D. Mazeas, et al., Heterocycles 1999, 50, 1065.) (213 mg, 1.0 mmol), L-BOC-tryptophanal (290 mg, 1.0 mmol) and piperidine (40 muL) in ethanol was refluxed for 2.5 hours and concentrated. The residue was triturated with dichloromethane (1 mL) and hexane (6 mL) and dried to provide the desired product (512 mg). MS (DCI/NH3) m/e 483, 485 (M+H)+.

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. 183208-34-6, 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 87674-15-5 ,Some common heterocyclic compound, 87674-15-5, molecular formula is C7H8FNO, 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 mixture of 1- (3-FLUOROPYRIDIN-4-YL) ETHANOL (10 g, 70.3 MMOL) and commercial activated Mn02 (8 G, 92.1 MMOL) in toluene (100 mL) were REFLUXED until disappearance of starting material. After cooling the mixture was filtered on a bed of celite, the cake washed with toluene and the organic phases concentrated to give 3-FLUORO-4-ACETYL pyridine (6.9 g, 70%) that was used directly in the next step.

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. 87674-15-5, 1-(3-Fluoropyridin-4-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMACIA ITALIA S.P.A.; WO2005/13986; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73112-16-0, 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.73112-16-0, name is 2,6-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, molecular weight is 250.92, as common compound, the synthetic route is as follows.

A dry round bottomed flask was charged with 2-aniino-4-cyclopropylpyridine (5.00 g, 31.7 mmol) and 2,6-dibromo-4-methylpyridine (7.95 g, 31.7 mmol). The reaction vessel was placed under an atmosphere of nitrogen (3x vacuum/N2 cycle), then 1,4-dioxane (lOOmL) was added and the mixture was degassed with a steady stream of nitrogen for 30 minutes. Sodium tert- butoxide (3.35 g, 34.8 mmol) and l,r-6/s(di-te^butylphospMno)ferrocene palladium dichlonde (0.49 g, 0.75 mmol) were added to the reaction flask, then the reaction was stirred at room temperature for 15 minutes then heated to 50 C for five hours. After cooling to room temperature for 14 hours, the resulting reaction mixture was poured into water (200 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were further washed with water and brine (200 mL portions). The organic phase was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield an oil. The crude product was purified by silica gel chromatography (0-30% ethyl acetate/hexanes) to give the title compound as a brown solid. lH NMR (600 MHz, DMSO-d6) delta 9.80 (s, IH), 8.06 (d, J= 5.3 Hz, IH), 7.70 (s, IH), 7.23 (s,IH), 6.92 (s, IH), 6.61 (dd, J= 1.4, 5.3 Hz, IH), 2.25 (s, 3H), 1.91 – 1.78 (m, IH), 1.09 – 0.98 (m, 2H), 0.82 – 0.66 (m, 2H).

Statistics shows that 73112-16-0 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromo-4-methylpyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; DI FRANCESCO, Maria Emilia; HAIDLE, Andrew, M.; OTTE, Ryan, D.; ELLIS, John Michael; CHILDERS, Kaleen Konrad; NORTHRUP, Alan, B.; YANG, Liping; WO2012/154520; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3430-18-0, 2,5-Dibromo-3-methylpyridine, 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, 3430-18-0, blongs to pyridine-derivatives compound. Product Details of 3430-18-0

A) 5-bromo-2-methoxy-3-methyl-pyridine: A suspension of 235-dibromo-3-methylpyridine (2.08 g, 8.3 mmol) in a 2 M solution of sodium methoxide in methanol (17 mL) was heated by single node microwave irradiation at 120 C for 40 minutes. The reaction mixture was poured onto a mixture of ice and 1 M aqueous hydrochloric acid and extracted with two portions of dichloro- methane. The combined organic layers were dried, filtered and concentrated in vacuo to give 1.57 g (89 %) of the sub-title compound which was used without further purification. 1H NMR (400 MHz; chloroform-d as solvent and internal reference) delta(ppm) 8.02 (d, IH, J= 2.3 Hz), 7.45 – 7.47 (m, IH), 3.92 (s, 3H), 2.16 (broad s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3430-18-0, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2007/8146; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 24059-83-4, 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 24059-83-4, name is Methyl 3-methoxypyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Compound 3-Methoxy-2-picolinic acid methyl ester (261 mg, 1.56 mmol),Sodium hydroxide (281 mg, 7.03 mmol) was dissolved in methanol (9 ml) and water (6 ml).Stir at room temperature for 1.5 hours. Spin down the solvent, add water to dissolve,Ethyl acetate was extracted 5 times, and the organic phases were combined and spin-dried to give the next reaction.

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 24059-83-4, Methyl 3-methoxypyridine-2-carboxylate.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Zhang Fenghua; Huang Shaoxu; (19 pag.)CN103539731; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem