Pyridine-derivatives

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. 1180132-17-5, name is 5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine. A new synthetic method of this compound is introduced below., Computed Properties of C12H20N4

General procedure: To a solution of 5a (0.10 g, 0.33 mmol) and 9a (0.07 g, 0.33 mmol) in 1,4-dioxane (2 mL), were added Cs2CO3 (0.21 g, 0.65 mmol), Pd2(dba)3 (0.03 g, 0.03 mmol) and XantPhos (0.03 g, 0.06 mmol). The mixture was heated to 120 C for 60 min with microwave, then cooled to room temperature, diluted with water (10 mL), and extracted with DCM (40 mL × 3). The combined organic layers were washed with water (40 mL) and brine (40 mL), dried over anhydrous Na2SO4, concentrated under vacuum, and purified by silica gel column chromatography (DCM / MeOH = 20:1) to give compound 10a (0.02 g, 12.40%) 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, 1180132-17-5, 5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine.

Reference:
Article; Wang, Yan; Liu, Wen-Jian; Yin, Lei; Li, Heng; Chen, Zhen-Hua; Zhu, Dian-Xi; Song, Xiu-Qing; Cheng, Zhen-Zhen; Song, Peng; Wang, Zhan; Li, Zhi-Gang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 5; (2018); p. 974 – 978;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16498-81-0 , The common heterocyclic compound, 16498-81-0, name is 2-Methoxynicotinic acid, molecular formula is C7H7NO3, 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.

Add 100 ml of water and 20 g of 2-methoxynicotinic acid to a 250 ml three-necked flask, then add 32 g of NBS.After 16 hours of reaction at a temperature of 20-25 degrees, a sample was taken for HPLC detection, and the reaction was terminated when HPLC detected that the starting material was less than 2%.After the end of the reaction, the mixture was filtered, and the solid was dried to give the product 2-methoxy-5-bromonicotinic acid, weight: 26.36 g, yield 87%.

The synthetic route of 16498-81-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Huichuan Bio-pharmaceutical Technology Co., Ltd.; Tang Bengang; He Weihua; (16 pag.)CN109503473; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 162102-79-6, Adding some certain compound to certain chemical reactions, such as: 162102-79-6, name is Dimethyl 4-bromopyridine-2,6-dicarboxylate,molecular formula is C9H8BrNO4, 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 162102-79-6.

(2) Synthesis of 4-bromo-6-(methoxycarbonyl)pyridine-2-carboxylic acid A mixture of 6.09 g of dimethyl 4-bromopyridine-2,6-dicarboxylate, 1.08 g of potassium hydroxide, 200 ml of methanol and 20 ml of methylene chloride was stirred at room temperature for 3 hours, and 200 ml of diethylether was added thereto. The resulting white solid was filtered, and then washed with ether. The obtained white solid was dissolved in water, and then 12 ml of hydrochloric acid (2 M) was added thereto. The resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo to give the title compound.

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. 162102-79-6, Dimethyl 4-bromopyridine-2,6-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP2017279; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 916325-85-4, 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, 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, Computed Properties of C7H4BrN3O2, blongs to pyridine-derivatives compound. Computed Properties of C7H4BrN3O2

To a solution of 5-bromo-1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (XVIII) (0.242 g, 1 mmol) in dry DMF (5 mL) was added CDI (0.178 g, 1.1 mmol) and heated for 3 h at 65 C. under nitrogen. The solution was cooled to room temperature and N,O-dimethyl hydroxylamine hydrochloride (0.107 g, 1.1 mmol) was added to the solution. The solution was again heated for 3 h at 65 C. under nitrogen. The solution was cooled and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM, washed successively with a 10% HCl solution, a saturated aqueous NaHCO3 solution and brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to produce 5-bromo-N-methoxy-N-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxamide (XIX) as a white solid (260 mg, 0.91 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 3.55 (s, 3H), 3.78 (s, 3H), 8.59 (d, J=3.01 Hz, 1H), 8.67 (d, J=3.01 Hz, 1H); ESIMS found for C9H9BrN4O2 m/z 285.4 (M+H).

The synthetic route of 916325-85-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark; US2013/296302; (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.89-00-9, name is Pyridine-2,3-dicarboxylic acid, molecular formula is C7H5NO4, molecular weight is 167.1189, as common compound, the synthetic route is as follows.COA of Formula: C7H5NO4

Pyridine-2,3-dicarboxylic acid 43.1 (20 g, 121 mmol) was dissolved in methanol (400 ml) then concentrated sulfuric acid (12.9 ml, 242 mmol) was added and the mixture was stirredreflux for 18 h. The volatiles were removed, and the liquid poured carefully into saturatedsodium carbonate. The pH was adjusted to 7 with sodium carbonate then extracted threetimes with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered andevaporated to provide compound 43.2 (19.5 g, 83percent) as an oil. 1H NMR (CDCI3, 300 MHz)3.96 (5, 3H), 4.04 (5, 3H), 7.50 (dd, 1H), 8.17 (d, 1H), 8.76 (d, 1H). UPLC (CSH 2-50percent)0.57 (196 [M+H]) 99percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89-00-9, Pyridine-2,3-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF SHEFFIELD; RICHARDS, Gareth; SKERRY, Timothy, M.; HARRITY, Joseph, P.A.; ZIRIMWABAGABO, Jean-Olivier; TOZER, Matthew, J.; GIBSON, Karl, Richard; PORTER, Roderick, Alan; BLANEY, Paul, Matthew; GLOSSOP, Paul, Alan; (369 pag.)WO2018/211275; (2018); 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. 16063-69-7, name is 2,4,6-Trichloropyridine, the common compound, a new synthetic route is introduced below. name: 2,4,6-Trichloropyridine

A mixture of 2,4,6-trichloropyridine (2.22 g, 12.20 mmol), methyl trans-4-aminocyclohexanecarboxylate hydrochloride (2.6 g, 13.42 mmol) and cesium carbonate (6.74 g, 48.8 mmol) in DMF (30 mL) was stirred in a sealed tube at 150 C. After 5.5 hours, the crude was poured on water (30 mL) and EtOAc (30 mL). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated. Purification of the residue by flash chromatography (hexanes/ethyl acetate 15% to 30% ethyl acetate) gave the title compound (1.02 g, 28%) as a yellow solid.LRMS (m/z): 303/305 (M+1)+.1 H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.24 (m, 4H), 1.6 (m, 2H), 2.11 (m, 2H), 2.31 (m, 1 H), 3.26 (m, 1 H), 3.69 (s, 3H), 4.32 (d, J = 7.3 Hz, 1 H), 6.34 (s, 2H)

The synthetic route of 16063-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Forns Berenguel, Maria Pilar; Castillo Mcquade, Marcos; Erra Sola, Montserrat; Mir Cepeda, Marta; EP2441755; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 78607-36-0, Adding some certain compound to certain chemical reactions, such as: 78607-36-0, name is 2-Chloro-3-iodopyridine,molecular formula is C5H3ClIN, 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 78607-36-0.

A mixture of 2-chloro-3-iodopyridine (400 mg , 1.67 mmol ), 2-methylpiperazine (200 mg, 2.0 mmol), sodium tert-butoxide (224 mg, 2.3 mmol), 9,9-dimethyl-4,5-bis(diphenyl- phosphino)Xanthen (48 mg, 0.08 mmol) and tris(dibenzylideneacetone) palladium (38 mg, 0.04 mmol) in toluene (6 mL) was heated at 110C for 18 hours. The mixture was poured out into water, extracted with EtOAc, the mixture was filtered through a short pad of Celite, the organic layer was separated, washed with water and brine, dried (MgS04), evaporated till dryness and the residue was carried out by flash chromatography over silica gel (grace, 40 g,CH2Cl2/MeOH/NH4OH 95/5/0.5) The pure fractions were collected and evaporated to dryness to afford 155 mg (44%) of intermediate (8).

According to the analysis of related databases, 78607-36-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; GUILLEMONT, Jerome Emile Georges; LANCOIS, David Francis Alain; MOTTE, Magali Madeleine Simone; LARDEAU, Delphine Yvonne Raymonde; BALEMANS, Wendy Mia Albert; ROYMANS, Dirk Andre Emmy; WO2015/14836; (2015); 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. 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Methyl 5-bromo-2-chloronicotinate

Compound WX069-1 (7.00 g, 27.95 nmol) wasdissolved in dimethyl sulfoxide solution (50.00 mE) at roomtemperature, followed by the addition of cesium fluoride(8.00 g, 52.67 mmol) at room temperature. The reactionmixture was heated to 550 C. and stirred for 14 hours. Afterthe reaction, the mixture was cooled to room temperature,quenched with saturated brine (10 mE), diluted with water(50 mE) and extracted with ethyl acetate (20 mLx3). Thecolunm c1omatography (eluent: petroleum ether/ethylorganic phases were separated, washed with water (50mEx2) and dried over anhydrous sodium sulfate, followedby filtration. The filtrate was concentrated under reducedpressure. The obtained residue was isolated by silica gelacetate1 00/1 – 100/15, volume ratio) to obtain the targetproduct WX069-2. ?H NMR (400 MHz, CDC13) oe: 8.64-8.31 (m, 2H), 3.98 (s, 3H).

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, 78686-79-0, Methyl 5-bromo-2-chloronicotinate.

Reference:
Patent; SHIJIAZHUANG SAGACITY NEW DRUG DEVELOPMENT CO., LTD.; LUO, Yunfu; YANG, Chundao; LEI, Maoyi; LIU, LING; HU, Guoping; LI, Jian; CHEN, Shuhui; US2019/177318; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 78607-36-0, 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.78607-36-0, name is 2-Chloro-3-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.

Example 1 :N-(2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamideStep 1 :2-Chloro-4-iodonicotinaldehydeA mixture of 2-chloro-3-iodopyridine (5.0 g, 21 mmol) in dry THF (30 mL) was slowly added to a cold (-78 C) solution of lithium diisopropylamide (15 mL, 30 mmol) in dry THF (50 mL). The resulting mixture was stirred for 3 h at this temperature. Ethyl formate (4.0 g, 54 mmol) was then added. Stirring was continued for 1.5 h at the same temperature. Water (10 mL) was added to quench the reaction, and then the resulting mixture was warmed to room temperature. 2M HC1 (50 mL) was added and then the THF was removed under reduced pressure. The aqueous residue was extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were washed with brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified on silica gel (diethyl ether: petroleum ether = 1 : 4) to give the desired product 2-chloro- 4-iodonicotinaldehyde as a yellow solid (3.0 g, 54% yield). NMR (500 MHz, CDC13): delta 10.22 (s, 1H), 8.09 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 78607-36-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; GOODACRE, Simon; LAI, Yingjie; LIANG, Yun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/66061; (2012); 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. 97483-77-7, name is 5-Bromopicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Bromopicolinonitrile

The organically modified hectorite-loaded ionic liquid material prepared by the first embodiment of the present invention (abbreviated as MHIL) is used as a catalyst for catalytic condensation to prepare an intermediate for the treatment of diabetes drugs 5-[(3R)-3-methylperazine Pyrazin-1-yl]pyridine-2-carbonitrile (CN 101400653A),The reaction is shown in Scheme3:5-bromo-2-cyanopyridine (10 mmol, 1.81 g) under nitrogen atmosphere,Catalyst MHIL (0.36g, 20wt%),(R)-(-)-2-methylpiperazine (1.3 g, 13 mmol) was placed in 20 ml of dimethyl sulfoxide at 100-110 C. After 8 h, the reaction liquid was HPLC-detected for substrate 5-bromine- 2-cyanopyridine was not detected. The catalyst was filtered to remove MHIL. The filtrate was added with 20 ml of a 3 M% aqueous solution of methylamine, and then extracted twice with 20 ml of dichloromethane. The methyl chloride layer is concentrated under reduced pressure5-[(3R)-3-methylpiperazin-1-yl]pyridine-2-carbonitrile 1.88 g, yield 93%, HPLC purity 99.86%, LC-MS: m/z = 203.1 [M +H].The organic modified hectorite-loaded ionic liquid material prepared by the invention (abbreviated as MHIL) is used as a catalyst for preparing an intermediate for the treatment of diabetes drugs 5-[(3R)-3-methylpiperazin-1-yl] Pyridine-2-carbonitrile does not require the addition of precious metal palladium as compared to CN 101400653A, and the yield is significantly improved.Although the embodiments of the present invention have been described in detail, it is understood that various changes, modifications and changes may be made in the embodiments of the present invention without departing from the spirit and scope of the invention.

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, 97483-77-7, 5-Bromopicolinonitrile.

Reference:
Patent; Zheng Chuanhua; Lu Xueling; Zhang Lei; (10 pag.)CN109369517; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem