Month: April 2022

Application of 109306-86-7, 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.109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.

Add 2g of magnesium turnings, one iodine, a small amount of tetrahydrofuran (THF), and a small amount of 2-(2-bromophenyl)pyridine in a 500ml three-necked flask.After the reaction was initiated, 200 ml of a solution of 2-(2-bromophenyl)pyridine (19 g) in tetrahydrofuran (THF) was slowly added dropwise.After refluxing until the magnesium dust disappeared, 15 g of a solution of compound 3 in THF was added dropwise, 100 ml.The reflux reaction was continued for 8 hours, then the temperature was lowered to room temperature, and 2N hydrochloric acid was added to quench the reaction.The solvent was evaporated under reduced pressure, and 300 ml of acetic acid was added to the obtained solid, and the mixture was heated to reflux for 2 hours.The solvent was removed by filtration at room temperature.After the obtained white solid was dissolved in 100 THF, an equal amount of methanol was slowly added.The white solid product was precipitated to 16.3 g, and the yield was 72.6%.

Statistics shows that 109306-86-7 is playing an increasingly important role. we look forward to future research findings about 2-(2-Bromophenyl)pyridine.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Liu Kaipeng; Yang Yan; Yang Dandan; Zhang Hongke; Gao Renxiao; (25 pag.)CN108948030; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1033772-26-7, 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. 1033772-26-7, name is Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate, molecular formula is C8H7N3O2, 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.

To a solution of 1 H-pyrazolo[3,4-c]pyridine-5-carboxylic acid, methyl ester (1.5 g, 8.5 mmol) in THF (350 mL) at 0 0C was added LAH (958 mg) in two portions. The reaction was stirred at 0 0C for 1.5 hr, and at rt for 1 hr. The reaction was quenched with con. NaOH at 0 0C, and the solid was filtered off and washed with MeOH. The filtrate was concentrated. Purification by column afforded 1 H-pyrazolo[3,4-c]pyridine-5-methanol (1.23 g, 96%).

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 1033772-26-7, Methyl 1H-pyrazolo[3,4-c]pyridine-5-carboxylate.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2008/71451; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73672-37-4, 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. 73672-37-4, name is Ethyl 2-oxo-2-(pyridin-3-yl)acetate. A new synthetic method of this compound is introduced below.

Reference Example 36 A mixture of ethyl 3-pyridylglyoxylate (6.00 g), hydroxylamine hydrochloride (2.79 g), sodium acetate (4.13 g) and ethanol (80 ml) was heated to reflux for 15 hours. The reaction mixture was concentrated, water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate to obtain ethyl E-2-hydroxyimino-2-(3-pyridyl)-acetate (3.30 g, yield 51%) as colorless crystals. m.p. 172-173 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73672-37-4, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6251926; (2001); B1;,
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. 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H8BrNO2

Into a vial was weighed methyl 5-bromo-4-methylpicolinate (1.00 g, 4.35 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (181 mg, 0.217 mmol), bis(pinacolato)diboron (1.21 g, 4.78 mmol), and potassium acetate (1.28 g, 13.0 mmol). Under nitrogen, anhydrous 1,4-dioxane (11 mL) was added and the vial was sealed. The reaction mixture was stirred at 100 C. for 18 h. After cooling to rt, the reaction mixture was concentrated and the residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10) to afford 756 mg of crude aryl pinacolboranate intermediate (contaminated with pinacolborane by 1H NMR). Combining this intermediate (323 mg, ?1.17 mmol) with (+-)-(1S,2S)-N-(8-(bis(2,4-dimethoxybenzyl)amino)-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (500 mg, 0.777 mmol), chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (32.8 mg, 0.0389 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (18.9 mg, 0.0389 mmol), and potassium phosphate tribasic monohydrate (554 mg, 2.33 mmol) in a vial, tetrahydrofuran (3.9 mL) and water (0.7 mL) were added under nitrogen and the vial was sealed and stirred at 80 C. for 19 h. The reaction mixture still contained starting material and so an equal aliquot of catalyst, ligand and water, as well as potassium phosphate tribasic monohydrate (184 mg, 0.777 mmol) and crude aryl pinacolboranate (215 mg, ?0.77 mmol) were added and stirred at 80 C. for 3 days. The mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10). The crude compound thus obtained was a yellow oil that contained the product according to HPLC-MS.

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, 886365-06-6, Methyl 5-bromo-4-methylpicolinate.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58602-02-1, 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. 58602-02-1, name is 2,6-Difluoro-3-nitropyridine, molecular formula is C5H2F2N2O2, 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.

b 2-(Ethylamino)-6-fluoro-3-nitropyridine To a solution of 2,6-difluoro-3-nitropyridine (45.7 g, 285 mmol) in THF (500 mL) at -40 C. was added drop-wise a solution of ethylamine (25.7 g, 570 mmol) in THF (250 mL). After 30 min, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated. The resulting yellow solid was purified by flash chromatography (15% EtOAc in hexane) to give the title compound (43.2 g, 82% yield) as a yellow solid.

According to the analysis of related databases, 58602-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Simoneau, Bruno; US2002/28807; (2002); 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. 193274-02-1, name is tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate

A clean, nitrogen purged reactor was charged with methylene chloride (471 L) and 2,3,3a,4,6,7-hexahydro-2-methyl-3-oxo-3a-(phenylmethyl)-5H-pyrazolo[4,3-c]pyridine-5-carboxylic acid 1,1-dimethylethyl ester (prepared according to Preparation Five, Step E, 47.0 kg, 1.0 eq.). The mixture was agitated and cooled to between -5C and 5C. The reaction mixture was slowly charged with triflouroacetic acid (117 kg, 7.5 eq.). The reaction mixture was warmed to a temperature between 20C and 30C and stirred for 12 to 15 hours. The reaction mixture was quenched by slow addition of an aqueous solution of 10% sodium carbonate (486 L, 0.5 eq.) at a temperature between 5C and 15C. The organic layer was separated and the aqueous layer extracted with methylene chloride (19 L). A mixture of acetone (456 L), water (56.4 L), and L-tartaric acid (22.6 kg, 1.1 eq.) was prepared in a second reactor. The tartaric acid mixture was combined with the organic layers at a temperature between 20C and 25C. The resulting slurry was heated to a temperature between 35C and 45C and stirred for 8 to 18 hours (overnight). When the reaction was judged to be complete, the slurry was cooled and granulated at a temperature between 0C and 10C for three to four hours and filtered. The product cake was washed with a mixture of acetone (40 L) and water (4.5 L). The product was dried under vacuum using only mild heat (applied if evaporation of acetone results in cooling). A yield of 37.7 kg of (3aR)-2,3a,4,5,6,7-hexahydro-2-methyl-3a-(phenylmethyl)-3H-pyrazolo[4,3-c]pyridin-3-one, (2R,3R)-2,3-dihydroxybutanedioate (1:1) was obtained (70.1% yield).

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, 193274-02-1, tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate.

Reference:
Patent; Pfizer Products Inc.; EP1031575; (2000); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 885168-04-7, 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.885168-04-7, name is 5-Bromo-3-chloropicolinaldehyde, molecular formula is C6H3BrClNO, molecular weight is 220.4511, as common compound, the synthetic route is as follows.

To a solution of Compound 1 (10 g) in methylene chloride (200 mL) were added oxalyl chloride (4.43 mL) andN,N-dimethylformamide (0.16 mL) at room temperature, and the mixture was stirred at room temperature for 2 hours.The reaction solution was concentrated under reduced pressure, the residue was dissolved in tetrahydrofuran (50 mL),and this was added dropwise to a suspension of thiosemicarbazide (3.85 g) and pyridine (75 mL) under ice cooling over10 minutes. After dropwise addition, the mixture was stirred at room temperature for 2 hours and concentrated underreduced pressure. The residue was dissolved in a 2N aqueous sodium hydroxide solution (210 mL), and heated at refluxfor 16 hours. The reaction solution was ice cooled and neutralized with concentrated hydrochloric acid (35 mL). Thedeposit was collected by filtration and washed with water and methanol. The obtained solid was suspended and washedin diethyl ether (50 mL), collected by filtration and dried at 50 C under reduced pressure to obtain Compound 2 (9.46g) as a beige solid.MS (m/z): 291/293/295 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 885168-04-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; SARUTA, Kunio; HAYASHI, Norimitsu; SAKURAI, Osamu; SAWAMOTO, Hiroaki; OBOKI, Eri; EP2862856; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 145255-19-2, 5-Aminopyridine-2-carboxamide, 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 5-Aminopyridine-2-carboxamide, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Aminopyridine-2-carboxamide

EXAMPLE 238: 4-[4-(6-CarbamoyIpyridin-3-ylamino)-7No.-pyrrolo[2,3-rf]pyriraidin-6-yl]-3,6-dihydro-2JHr-pyridme-l-carboxylic acid tert-butyl ester; .NH2^»[673] Into the DMF (ImL) solution of 4-(4-chloro-7No.-pyrrolo[2,3-J]pyrimidin-6-yl)-3,6-dihydro-2/ir-pyridine-l-carboxylic acid tert-butyl ester (122mg, 0.363mmol) wasadded t-BuOK (1M in ^-BuOH, 0.726mL, 0.726mmol) dropwise at RT under N2 over 5min.The mixture was then put in an ice/water bath and stirred for lOmin. After that time, theDMF (ImL) solution of 5-aminopyridine-2-carboxylic acid amide (99.5mg, 0.726mmol) wasadded into the above mixture dropwise. The reaction mixture was warmed to RT.Pd2(dba)3-CHCl3 (9.4mg, 2.5%eq.) and^(+)-BINAP (22.6mg, O.leq.) were added, and themixture was heated at 100C for 24h. The mixture was filtered and the filtrate wasconcentrated in vacua. The crude was submitted to MS directed purification. A brown oilwas obtained that was purified further by HPLC to obtain the title compound as an off-whitesolid. ‘H NMR (DMSO-dft 400 MHz): 5 = 1.50 (s, 9 H), 2.50 (m, 2 H), 3.64 (t, 2 H, J= 5.6Hz), 4.12 (bra, 2 H), 6.50 (bra, 1 H), 6.88 (s, 1 H), 7.53 (d, 1 H, J= 4.2 Hz), 8.04 – 8.05 (m, 1H), 8.08 (d, 1 H, J= 8.8 Hz), 8.44 (s, 1 H), 8.68 (dd, 1 H, /= 2.4 & 8.4 Hz), 9.12 (d, 1 H, J=2.4 Hz), 9.91 (s, 1 H), 12.18 (s, 1 H). MS (ES+): m/z 436.10 (100) [MET]. HPLC: fe = 2.75min (ZQ2000, polar_5 min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,145255-19-2, 5-Aminopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1443759-42-9, 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 1443759-42-9 as follows.

36.3: 4-Bromo-6-methoxy-pyridine-2-carboxylic acid methyl ester To a mixture of 3.47 mL (29.3 mmol) tert-butyl nitrite and 6.60 g (29.3 mmol) copper(II)bromide in 120 mL acetonitrile was added a solution of 3.33 g (18.3 mmol) 4-amino- 6-methoxy-pyridine-2-carboxylic acid methyl ester in 30 mL acetonitrile dropwise at 40 C. This mixture was stirred at 80 C for 1 h, then poured into ice water. The precipitate was filtered off, washed with water and dried. The crude material was purified by flash chromatography (PE/EtOAc = 4/1 -> 3/1). yield: 2.50 g (56 %) + ESI-MS: m/z = 246 (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,1443759-42-9, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; WO2013/87805; (2013); 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.251101-36-7, name is 3-Methylisonicotinamide, molecular formula is C7H8N2O, molecular weight is 136.15, as common compound, the synthetic route is as follows.HPLC of Formula: C7H8N2O

3-Methyl-4-cyanopyridine (123) Phosphorus oxychloride (100 mL, 1.1 mol) was slowly added to the crude amide 122 (15 g, 0.11 mol) while cooling the mixture in an ice bath. The resulting solution was heated at reflux for 24 h. The reaction mixture was cooled to room temperature and the excess phosphorus oxychloride was removed under reduced pressure. Crushed ice (150 g) was slowly added to the oily residue, and the solution was neutralized with saturated ammonium hydroxide. The crude product was extracted with chloroform (3*100 mL). The combined extracts were filtered through a layer of silica gel, washing with extra portions of chloroform. The filtrates were evaporated to dryness to yield 123 as colorless crystals (12 g, 90%): mp 45-47 C. (lit. (J. Med. Chem. 2000, 43, 3168-3185) mp 50 C.). 1H NMR (300 MHz, CDCl3) delta 8.66 (s, 1H), 8.59 (d, J=5.0 Hz, 1H), 7.45 (d, J=5.0 Hz, 1H), 2.54 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,251101-36-7, 3-Methylisonicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; CUSHMAN, Mark S.; KISELEV, Evgeny A.; MORRELL, Andrew E.; US2014/18360; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem