Pyridine-derivatives

Synthetic Route of 149806-06-4 ,Some common heterocyclic compound, 149806-06-4, molecular formula is C6H4BrNO, 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.

Reagents: i) Methaneboronic acid, 16%; ii) Ethyl acrylate ; iii) NaOH, 35% yield for the last two steps.LC/MS data of 2805 – Calculated MW is 177; observed (the peak at 11.2 min, TIC): 178 [M+H].Gradient: 0-5 min: 5% ACN; 5-20 min: 5-10% ACN; 20-30 min: 10-98%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,149806-06-4, its application will become more common.

Reference:
Patent; TRUSTEES OF TUFTS COLLEGE; WO2008/16968; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 959616-64-9, 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 959616-64-9 as follows.

[00672] Intermediate 73c: methyl 5-fluoro-6-methoxy-pyridine-3-carboxylate[00673] Triethylamine (1 .62mL, 11.61 mmol), tetrakis(triphenylphosphine)palladium(0) (0.45g, 0.3gmmol) and formic acid (0.44mL, 11 .61 mmol) were added to a flask containing a stirring solutionof methyl 2-chloro-5-fluoro-6-methoxy-pyridine-3-carboxylate (1 .7g, 7.74mmol) in DMF (1 7mL). The reaction mixture was then heated to 100 C and left to stir for 4 hours. The reaction mixture was left to cool before being filtered through celite and the solvent removed in vacuo. The residue was taken up in EtOAc (5OmL), water (5OmL) added and the organics extracted with further EtOAc (3 x 5OmL). The organic layers were combined, dried over Na2504, filtered and concentrated in vacuo. Theresidue was purified by column chromatography using an eluent of 0-50% EtOAc in heptane) toafford the desired product methyl 5-fluoro-6-methoxy-pyridine-3-carboxylate (590mg, 3.1 9mmol,41% yield) as a white solid.1H NMR (CDCI3,400MHz) O/ppm: 8.61 (1H, d, J= 1.9Hz), 7.88 (1H, dd, J= 10.4Hz, 1.9Hz), 4.09(3H, 5), 3.92 (3H, 5),MS Method 3: RT: 5.10 mm, 186.1 m/z [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,959616-64-9, its application will become more common.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7418-65-7, Adding some certain compound to certain chemical reactions, such as: 7418-65-7, name is 4-Aminonicotinic acid,molecular formula is C6H6N2O2, 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 7418-65-7.

(E)-[6-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]]-3-pyhdinecarboxylic acid (FT104)A suspension of (£)-3-(3,4-dimethoxyphenyl)-2-propenoic acid (1.0 g, 4.8 mmol) in CH2CI2 (10 mL) was treated with oxalyl chloride (1.6 ml_, 19 mmol). The solution was stirred at rt for 1 h and the solvent was removed under reduced pressure to give the acid chloride as a yellow solid. 4-Aminonicotinic acid (0.73 g, 5.3 mmol) was added to a solution of the acid chloride (4.8 mmol) in pyridine (5.0 mL) and the suspension was heated to reflux and stirred for 5 d. The solution was diluted with water and the precipitate was collected by filtration providing (£)-[6-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2- propenyl]amino]]-3-pyridinecarboxylic acid (0.25 g, 16%) as a colourless solid; mp 258- 260 0C; deltaH (500 MHz, DMSO-d6) 3.80 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 6.82 (d, J = 15.5 Hz, 1H1 CH=CHCO), 7.00 (d, J5.ibeta. = 8.0 Hz, 1 H, H5′), 7.23 (dd, J6.>beta. = 8.0, J2,6. = 2.0 Hz, 1 H1 H6′), 7.33 (s, J2, 6. = 2.0 Hz, 1H, H2′), 7.62 (d, J = 15.5 Hz, 1H, CH=CHCO), 8.60 (d, J5,6 = 8.0 Hz, 1 H, H5), 8.63 (d, J5j6 = 8.0 Hz, 1H, H6), 9.03 (s, 1H, H2); HRMS (ESI) calculated for C17H14N2O4 [M+H]+ 329.1132, found 329.1129; vmax 1140, 1262, 1488, 1623, 2938, 3543 cm”1.

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. 7418-65-7, 4-Aminonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FIBROTECH THERAPEUTICS PTY LTD; WILLIAMS, Spencer John; ZAMMIT, Steven; KELLY, Darren James; JAMES, Ian William; WO2010/144959; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 787596-41-2, name is Methyl 2-chloro-3-methylisonicotinate, molecular formula is C8H8ClNO2, 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. Product Details of 787596-41-2

To a solution of methyl 2-chloro-3-methylisonicotinate (6.00 g, 32.32 mmol) in CC14 (30 mL) was added NBS (6.06 g, 33.94 mmol) and BPO (780 mg, 3.23 mmol). After addition, the reaction mixture was heated to reflux for 3 h. TLC indicated that starting material was consumed. Then, it was cooled to ambient temperature and the resulting precipitate wasremoved by filtration, washed by CC14 (5 mL). The filtrate was concentrated in vacuo to give the crude product methyl 3-(bromomethyl)-2-chloroisonicotinate as a yellow oil, which was used in next step without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 787596-41-2.

Reference:
Patent; SHANGHAI METON PHARMACEUTICAL CO., LTD; YANG, Jibin; (102 pag.)WO2018/10142; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 123148-66-3, 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 123148-66-3 as follows.

Manganese dioxide (1.04 g) was added to a solution of (2-methoxypyridin-4-yl)methanol (417 mg) in ethyl acetate (5 mL), followed by refluxing for 1.5 hours. Manganese dioxide (1.04 g) was added thereto, followed by refluxing for 1.5 hours. The reaction mixture was cooled to room temperature, the insoluble materials were filtered off, and the solvent was distilled off under reduced pressure. The obtained residues were purified by silica gel column chromatography (hexane:ethyl acetate=9:1?4:6), whereby 2-methoxyisonicotinic aldehyde (260 mg) was obtained as a colorless oily material

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,123148-66-3, its application will become more common.

Reference:
Patent; FUJIFILM Corporation; KUBO, Yohei; ANDO, Makoto; TANAKA, Hidehiko; OSAKA, Shuhei; MATSUMOTO, Takuya; NAKATA, Hiyoku; TERADA, Daisuke; NITABARU, Tatsuya; (379 pag.)US2016/168139; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14482-51-0, 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. 14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, 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 microwave vial is added 4-methyl-3-(2,2,6,6-tetramethyl-3,5-dioxo-tetrahydropyran-4- yl)phenylboronic acid (200 mg, 0.657 mmol), 2-bromo-3,5-dichloropyridine (149 mg, 0.657 mmol), palladium acetate (3.7 mg, 0.0164 mmol), tris(3-sulfophenyl)phosphine trisodium salt (22 mg, 0.0394 mmol) and potassium phosphate (697 mg, 3.28 mol), followed by a degassed solvent mixture of water/acetonitrile (1.6 ml, 2:1 ratio). The mixture is flushed with nitrogen then stirred at ambient temperature for 5 minutes before heating at 1600C under microwave irradiation for 15 minutes. After cooling to room temperature the reaction is partitioned between 2M aqueous hydrochloric acid and dichloromethane, and the organic phase is separated. The aqueous phase is further extracted with dichloromethane and all organic fractions are combined then evaporated. The residue is purified by preparative reverse phase HPLC to give 4-[5-(3,5-dichloropyridin-2-yl)-2-methylphenyl]-2, 2,6,6- tetramethylpyran-3,5-dione (113 mg).

According to the analysis of related databases, 14482-51-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2008/71405; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58530-53-3, 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 58530-53-3, name is 2,4-Dibromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 21i 4-Bromo-2-cyclopropylpyridine To a solution of 2,4-dibromopyridine (3.00 g, 12.66 mmol) in dry tetrahydrofuran (10 mL) under an atmosphere of argon was added tetrakis(triphenylphosphine)palladium(0) (0.435 g, 0.38 mmol). The reaction vessel was put in a water-bath (~20 C.) and cyclopropylzinc(II) bromide, 0.5M in tetrahydrofuran (30.1 mL, 15.05 mmol) was added is over a period of 10 minutes. The reaction mixture was stirred at 20 C. for 80 minutes. More cyclopropylzinc(II) bromide, 0.5M in tetrahydrofuran (7.52 mL, 3.76 mmol) was added and the reaction mixture was stirred for another 40 minutes before it was poured into saturated aqueous NaHCO3 (100 mL) and diluted with EtOAc (100 mL). The layers were separated and the aqueous layer extracted with EtOAc (50 mL). The organics were combined, dried (Na2SO4), filtered and the solvent was evaporated at reduced pressure. The crude was purified by flash chromatography on silica gel to afford 2.12 g (85%) of the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 8.25 (d, 1H) 7.33 (d, 1H) 7.21 (dd, 1H) 1.93-2.06 (m, 1H) 0.98-1.08 (m, 4H); MS (CI+) m/z 198, 200 [M+H]+

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 58530-53-3, 2,4-Dibromopyridine.

Reference:
Patent; ASTRAZENECA AB; US2010/125082; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3510-66-5, 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. 3510-66-5, name is 2-Bromo-5-methylpyridine, molecular formula is C6H6BrN, 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.

172 g of thus obtained 2-bromo-5-methylpyridine was dissolved in 1.3 l of carbon tetrachloride, and the system was then heated. At the time refluxing begain (at 77 C.), chlorine gas was bubbled into the system with ultraviolet light irradiation. After a lapse of 5 hours, the completion of the reaction was confirmed by gas chromatography, and the system was cooled and air was bubbled into the system to expel the unreacted chlorine. The system was washed with water several times and dried over anhydrous sodium sulfate. Then, the carbon tetrachloride was distilled off, and the system was allowed to cool. The solid crystals thus-obtained were washed with n-hexane to obtain 152 g of 2-chloro-5-trichloromethylpyridine with a melting point of 51 to 54 C.

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 3510-66-5, 2-Bromo-5-methylpyridine.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US4184041; (1980); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 40473-01-6, 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. 40473-01-6, name is 2-Bromo-5-chloropyridine. A new synthetic method of this compound is introduced below.

Intermediate 1 : methyl delta-chloro^-pyridinecarboxylate To a solution of 2-bromo-5-chloropyridine (30.0 g, 155.9 mmol) in MeOH (280 ml.) was added Pd(OAc)2 (3.5 g, 10.8 mmol), dppf (17.3 g, 37.96 mmol), Et3N (42.0 ml_, 312 mmol). The resulting mixture was stirred at 500C under a CO atmosphere (15 psi) for 24 h, then concentrated under reduced pressure to give crude residue. This residue was partitioned between EtOAc (3 X 500 ml.) and water (300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel, by using 10:1 petroleum ether/EtOAc, afforded the title compound as a pale yellow solid (25 g, 93%): 1H NMR (400 MHz, CDCI3) delta ppm 8.60 (d, J = 1.60 Hz, 1 H), 8.01 (d, J = 8.40 Hz, 1 H), 7.75 (dd, J = 8.40, 2.40 Hz, 1 H), 3.92 (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,40473-01-6, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; CHRISTENSEN, Siegfried, Benjamin, IV; QIN, Donghui; CHEN, Shenglin; HUANG, Xing; LI, Di; LI, Fei; LI, Lei; LIN, Xiaojuan; LU, Shi; LU, Zhen; LV, Maoyun; WANG, Chuanning; WU, Chengde; XIAO, Mei; YU, Haiyu; ZHANG, Weina; ZHANG, Zhiliu; WO2010/141539; (2010); A1;,
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. 757978-18-0, name is 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

Into a 250 mL round bottomed flask were added 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (8.00 g, 40.6 mmol) and 120 mL dry THF. The solution was cooled in an ice bath at 0 C and NaH (2.40 g, 60.0 mmol) was added in three portions. After 20 min, />-toluenesulfonyl chloride (8.70 g, 45.63 mmol) was added, and the reaction mixture was allowed to warm to rt over 30 min. The reaction mixture was concentrated and hexanes was added to obtain a precipitate, which was collected and washed with ice cold 2M NaOH. The crude product was recrystallized from EtOAc/hexanes to afford 17.8 g (92%) of the title compound as a light tan powder. 1H-NMR (500 MHz, ^6-DMSO) delta 8.49 (d, J=2.5 Hz, 1H), 8.21 (s, 1H), 7.99 (d, J=2.0 Hz , 1 H), 7.98(d, J=8.5 Hz , 2H), 7.42 (d, J=8.5 Hz, 2H), 2.32(s, 3H); MS: m/z 476.8/478.8 [MH+].

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, 757978-18-0, 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2008/124849; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem