Category: pyridine-derivatives

Related Products of 72830-09-2, 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.72830-09-2, name is 2-Chloromethyl-3,4-dimethoxypyridinium chloride, molecular formula is C8H11Cl2NO2, molecular weight is 224.08, as common compound, the synthetic route is as follows.

4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenol (100 mg, 0.454 mmol), 1-1 (85 mg, 0.454 mmol), and 2C03 (157 mg, 1.136 mmol) were combined in a 50-mL round bottom flask with a stirbar. DMF (3.03 mL) was added, and the reaction mixture was heated to 90 C for 4 h. The reaction mixture was diluted with EtOAc (30 mL), and washed sequentially with sat. aq. NaHC03 (30 mL) and brine (30 mL). The combined organics were dried over MgS0 , filtered, and concentrated in vacuo to afford the title compound as a tan solid (155 mg, 78%, >85% pure), which was used in the subsequent step without further purification.

Statistics shows that 72830-09-2 is playing an increasingly important role. we look forward to future research findings about 2-Chloromethyl-3,4-dimethoxypyridinium chloride.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BRESLIN, Michael, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; WO2011/53559; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 108281-79-4, 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. 108281-79-4, name is 6-Bromo-[1,2,4]triazolo[4,3-a]pyridine, molecular formula is C6H4BrN3, 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.

In a 5 mL vial 6-bromo-[1,2,4]triazolo[4,3-a]pyridine (93 mg), 4-trifluoromethoxyphenylboronie acid (115 mg), and potassium carbonate (187 mg) were suspended in DMF (2 mL) that was previously degassed with nitrogen. Tetrakis(triphenylphosphine) palladium (20 mg) was added and the reaction mixture was heated in a microwave reactor at 150 C. for 30 min, filtered, and concentrated. The residue was subjected to gradient chromatography (MeOH/dichloromethane) to produce white powder, 56.4 mg (43% yield).1H NMR (400 MHz, CDCl3): delta 8.89 (s, 1H), 8.27 (br s, 1H); 7.89 (d, J=9.2 Hz, 1H); 7.59 (d, J=8.4, 2H); 7.52 (d, J=9.6 Hz, 1H); 7.36 (d, J=7.6, 2H).MS (ES+, m/z) 280.0 (base peak, M+H+); 581.0 (2M+Na+).

According to the analysis of related databases, 108281-79-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Palo Alto, Inc.; US2011/21521; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 19337-97-4 ,Some common heterocyclic compound, 19337-97-4, molecular formula is C8H7NO2, 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 (E)-3-(pyridin-3-yl)acrylic acid (37 mg, 0.25 mmol) in DMF (2 mL) was added EDCI (78 mg, 0.41mmol), HOBt (41 mg, 0.31 mmol), triethylamine (0.06mL, 0.41mmol), and compound 40a (65 mg, 0.2 mmol), and the reaction mixture was stirred for 4 h at room temperature. DMF was evaporated under reduced pressure. The residue was extracted with ethyl acetate (4 mL × 3). The combined organic layers were washed with saturated aqueous NaHCO3 solution, saturated aqueous NH4Cl solution and brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting mixture was purified by silica column chromatography to give the target compound 19 as white solid (45 mg, 50percent). 1H NMR (400 MHz, CDCl3) delta 8.76 (s, 1H), 8.57 (d, J = 4.2 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.65 (d, J = 15.7 Hz, 1H), 7.60 (s, 1H), 7.52 (s, 1H), 7.30 (t, J = 9.1 Hz, 3H), 7.23 (d, J = 7.7 Hz, 3H), 7.12 (d, J = 6.5 Hz, 3H), 6.47 (d, J = 15.7 Hz, 1H), 5.78 (s, 1H), 3.37 (dd, J = 13.2, 6.8 Hz, 2H), 2.63 (t, J = 7.3 Hz, 2H), 1.60 ? 1.52 (m, 4H), 1.30 (dt, J = 15.4, 7.6 Hz, 2H). 13C NMR (125 MHz, CDCl3) delta 165.4, 150.3, 149.1, 143.5, 139.1, 137. 7, 136.9, 134.6, 133.1, 130.7, 129.3, 128.9, 127.0, 125.4, 124.7, 123.8, 122.7, 122.1, 39.7, 35.1, 30.2, 29.3, 25.9. HRMS(ESI) m/z calculated for C25H28N3O3S [M + H]+: 450.1846, found 450.1846.

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. 19337-97-4, trans-3-(3-Pyridyl)acrylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Kuojun; Ni, Yong; Chen, Jiaxuan; Tu, Zhengchao; Wu, Xiaoxing; Chen, Dong; Yao, Hequan; Jiang, Sheng; Bioorganic and Medicinal Chemistry Letters; vol. 29; 12; (2019); p. 1502 – 1506;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 884495-39-0, 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 884495-39-0 as follows.

To 5-bromo-2-(methyloxy)-3-pyridinamine (18.93 g) in a round-bottom flask was added nitrogen-purged 1 ,4-dioxane (500 ml) followed by 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi- 1 ,3,2-dioxaborolane (47.4 g), potassium acetate (27.5 g) and Pd(dppf)CI2-CH2Cl2 adduct (7.61 g). The mixture was then stirred at 80 C under nitrogen for 2 h. The reaction mixture was allowed to cool then partitioned between ethyl acetate and water. The mixture was filtered through a celite pad and the aqueous layer extracted twice with ethyl acetate. The combined organics were washed with water, brine and dried over magnesium sulphate overnight. The residue was purified on 1.5 Kg Silica cartridge, using a 0 – 50 % ethyl acetate:DCM gradient over 10 column volumes. The appropriate fractions were combined and evaporated to dryness. The residue was triturated with cyclohexane, filtered and dried in vacuo to give the title compound as a light pink solid, 1 1.1 g. A second crop was obtained from the filtrate and after drying gave a further portion of the title compound as a light pink solid, 2.95g. LCMS (method B); Rt 0.91 = min, MH+ = 251 .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-39-0, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian Robert; DOWN, Kenneth David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie Nicole; JONES, Katherine Louise; JONES, Paul Spencer; LE, Joelle; LUNNISS, Christopher James; PARR, Nigel James; RITCHIE, Timothy John; ROBINSON, John Edward; SIMPSON, Juliet Kay; SMETHURST, Christian Alan Paul; WO2011/67365; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1990-90-5, Adding some certain compound to certain chemical reactions, such as: 1990-90-5, name is 3-Methylpyridin-4-amine,molecular formula is C6H8N2, 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 1990-90-5.

To a solution of 2-(5-chloro-2-fluorophenyl)-4-iodo-5,7-dihydrofuro[3,4-d]pyrimidine (80 mg, 0.21 mmol, 1 eq) in anhydrous dioxane (5 ml) was added Pd(OAc)2 (2 mg, 0.01 mmol, 0.05 eq) followed by BINAP (10 mg, 0.02 mmol, 0.075 eq), 4-amino-3- picoline (25 mg, 0.23 mmol, 1.2 eq) and Cs2CO3 (100 mg, 0.32 mmol, 1.5 eq). The EPO reaction mixture was heated to 80C for 15h. The reaction mixture was cooled to r.t. and filtered through Celite and the crude material was purified by flash column chromatography (9:l/ethyl acetate:hexane) to afford [2-(5-Chloro-2-fluorophenyl)-5,7- dihydrofuro[3,4-d]pyrimidin-4-yl]-(3-methyl-pyridin-4-yl)-amine, compound of formula (33) (20 mg, 26%) as a white solid

According to the analysis of related databases, 1990-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2006/35061; (2006); 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. 1050501-88-6, name is 2-Bromo-6-chloropyridin-3-amine, the common compound, a new synthetic route is introduced below. name: 2-Bromo-6-chloropyridin-3-amine

A mixture of tert-butyl methyl(prop-2-yl-1-yl)carbamate (612 mg, 3.62 mmol, Intermediate 11), 2-bromo-6-chloropyridin-3-amine (500 mg, 2.410 mmol, Fluorochem), copper I iodide (51 mg, 0.268 mmol, Sigma), PdCI2(dppf) (148 mg, 0.202 mmol, Manchester Organics) and TEA (0.504 ml_, 3.62 mmol, Sigma) in a sealed vial was degassed (purged and filled with nitrogen x 3) before adding anhydrous Tetrahydrofuran (THF) (10 ml_). The suspension was degassed by bubbling nitrogen through for 2 min. The reaction mixture was heated to 70 C for 17 hr. The reaction mixture was filtered through a 2.5g Celite SPE, eluting with ethyl actetate (30 ml.) and water (10 ml_). The reaction mixture was diluted with water (20 ml_), the aqueous extracted with ethyl acetate (3 x 30 ml_), combined organics washed with brine (20 ml_), dried through a hydrophobic frit and concentrated in vacuo and under nitrogen to give tert-butyl (3-(3-amino-6-chloropyridin-2-yl)prop-2-yn-1- yl)(methyl)carbamate (1.074 g, 2.360 mmol, 98 % yield) as a brown oil. 1H NMR (400 MHz, CHLOROFORM-d) d ppm 1.45 – 1.56 (m, 12 H) 3.00 (s, 3 H) 4.34 (s, 2 H) 6.96 – 7.13 (m, 2 H). LCMS (System B, UV, ESI) Rt = 1.08 min, [M+H]+ 240, 242

The synthetic route of 1050501-88-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BRAVI, Gianpaolo; HOBBS, Heather; INGLIS, Graham George Adam; NICOLLE, Simon; PEACE, Simon; (138 pag.)WO2019/115640; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6959-48-4, 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. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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 of4(1.00 eq.) in DMF was added K2CO3(1.20-2.00 eq.). The reaction was stirred at room temperature for 1 h, followed by the addition of the alkyl halide (1.00-1.10 eq.). The reaction was stirred at room temperature for 0.5-24 h, concentrated under reduced pressure and purified by flash column chromatography (silica gel, solvent system I: petroleum ether ramping to 100% EtOAc, or solvent system II: DCM ramping to DCM/MeOH = 97:3) to give the desired product.

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 6959-48-4, 3-(Chloromethyl)pyridine hydrochloride.

Reference:
Article; Diab, Sarah; Abdelaziz, Ahmad M.; Li, Peng; Teo, Theodosia; Basnet, Sunita K.C.; Noll, Ben; Rahaman, Muhammed H.; Lu, Jingfeng; Hou, Jinqiang; Yu, Mingfeng; Le, Bich T.; Albrecht, Hugo; Milne, Robert W.; Wang, Shudong; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 762 – 772;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14432-12-3, 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. 14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, 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.

Intermediate 252A: 2-chloro-5-iodopyridin-4-amine To a stirred solution of 2-chloropyridin-4-amine (5 g, 39 mmol) in DMF (50 mL) was added NIS (8.75 g, 39 mmol). The reaction mixture was then heated at 80 C for 3 h. The mixture was cooled and the DMF removed in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The organic layer was dried over Na2S04, filtered, and concentrated. The product was purified via column chromatography (10% EtO Ac/pet ether) to afford 2-chloro-5-iodopyridin-4-amine (4 g, 39% yield). LCMS: 254.8 (M+). Further elution with 12% EtO Ac/pet ether afforded 2- chloro-3-iodopyridin-4-amine (4 g, 39% yield).

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 14432-12-3, 4-Amino-2-chloropyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54221-95-3, 2-Acetylaminoisonicotinic 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, Product Details of 54221-95-3, blongs to pyridine-derivatives compound. Product Details of 54221-95-3

A mixture of (-)-1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (1.50 g, 5.12 mmol, Amine-1, single enantiomer), 2-acetamidoisonicotinic acid (1.01 g, 5.63 mmol), HBTU (2.33 g, 6.14 mmol) and triethylamine (3.57 mL, 25.6 mmol) in dichloromethane (51 mL) is stirred at room temperature for 15 hours. The reaction mixture is poured into water (50 mL) and extracted with dichloromethane (50 mL). The organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate to give 1.30 g (66percent yield) of the title compound as a white solid.1H-NMR (300 MHz, DMSO-d6) delta 10.6 (1H, s), 9.08 (1H, d, J = 8.1 Hz), 8.41-8.38 (2H, m), 8.18 (1H, d, J = 2.2 Hz), 7.82 (1H, dd, J = 8.4, 2.2 Hz), 7.43 (1H, d, J = 5.1 Hz), 6.96 (1H, d, J = 8.8 Hz), 5.14 (1H, m), 4.96 (2H, q, J = 9.2 Hz), 2.09 (3H, s), 1.47 (3H, d, J = 7.0 Hz), MS (ESI) m/z: 383 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54221-95-3, 2-Acetylaminoisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; RAQUALIA PHARMA INC.; YAMAGISHI, Tatsuya; KAWAMURA, Kiyoshi; ARANO, Yoshimasa; MORITA, Mikio; WO2012/53186; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67346-74-1, 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.67346-74-1, name is 3-Ethynylpyridin-2-amine, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

Reference Example 46 3-(3-(4-(5-Methyl-furan-2-ylmethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine; To a mixture of (4-(5-methyl-furan-2-ylmethyl)-phenyl)-acetohydroximoyl chloride (11 mg, 0.043 mmol) described in Manufacturing Example 46-1-6 and tetrahydrofuran (1 mL) were added 3-ethynyl-pyridin-2-ylamine (4.0 mg, 0.034 mmol) described in Manufacturing Example 1-2-3 and triethylamine (9.4 muL, 0.068 mmol) at room temperature, which was stirred for 3 hours at 45 C. The reaction mixture was cooled to room temperature, water was added at the same temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate_heptane=2:3) to obtain the title compound (5.1 mg, 41%).1H-NMR Spectrum (CDCl3) delta (ppm): 2.24 (3H, s), 3.90 (2H, s), 4.03 (2H, s), 5.53 (2H, br s), 5.85 (1H, d, J=2.9 Hz), 5.87 (1H, d, J=2.9 Hz), 6.26 (1H, s), 6.72 (1H, dd, J=5.0, 7.6 Hz), 7.21 (4H, s), 7.72 (1H, d, J=7.7 Hz), 8.12 (1H, dd, J=1.8, 4.9 Hz).

The chemical industry reduces the impact on the environment during synthesis 67346-74-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem