Pyridine-derivatives

Electric Literature of 915107-30-1, 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. 915107-30-1, name is Methyl 6-chloro-5-hydroxynicotinate. A new synthetic method of this compound is introduced below.

To a solution of methyl 6-chloro-5-hydroxypyridine-3-carboxylate (720 mg, 3.84 mmol) in DMF (10 mL) was added methyl iodide (635 mg, 4.46 mmol) at room temperature. The resulting solution was stirred for 8 h at room temperature and diluted with water (30 mL). The mixture was extracted with ethyl acetate (50 mL*3). The organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was concentrated under reduced pressure to yield methyl 6-chloro-5-methoxypyridine-3-carboxylate as yellow solid (600 mg, 66%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,915107-30-1, Methyl 6-chloro-5-hydroxynicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 94446-97-6, 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. 94446-97-6, name is 2-Bromo-3-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

This intermediate was generated by a modified procedure based on that disclosed in Viswanathan, R., et al., J. Am.Chem. Soc., 125, 163 (2003) and Synthesis 2, 330 (2005). A three neck round bottom flask with a stir bar was chargedwith I-5 (40.1 g, 135.7 mmol), I-7 (8.2 g, 13.6 mmol), powdered KOH (69.1 g, 1221.4 mmol), and DCM (600 ml).The opaque yellow suspension was cooled to -78C and the flask fitted with a dropping funnel. A suspension of I-4 (152.0 g, 610.7 mmol) in 400 ml DCM was transferred to the dropping funnel and added to the reaction at -78C over about 1 hr. The suspension in the dropping funnel would occasionally settle and the solid would be resuspended. After the end of the addition the funnel was rinsed with an additional 200 ml of DCM and the rinse was added to the reaction. After 10 hrs at -78C. the reaction was allowed to stir overnight as it warmed to room temperature. Analysis of the reaction by HPLC and TLC showed complete conversion of I-4. The reaction was diluted with 3 L of DCM transferred to a 15 L reactor and extracted 2 x 1 L of water. During the separation the organic phase appeared cloudy due to a solid formed from I-4. The organic phase was collected then washed with NaCl (satd.aqueous), dried over anhydrous sodium sulphate, filtered and concentrated to near dryness and purified by normal phase flash chromatography. A three solvent mobile phase was used for the separation; initially DCM/hexanes to elute the excess I-4, followed by EtOAc/Hexanes to elute the title compound (S)-tert-butyl 3-(2-bromopyridin-3-yl)-2-((diphenylmethylene)amino)propanoate (I-8) obtained as a yellow solid (23.1 g, 226.0 mmol, 37%). H1 NMR (400 MHz, CDCl3) delta 8.20(1H, dd, J=4.2 Hz), 7.60(2H, d, J=8 Hz), 7.56(1H, dd,J=4.2 Hz), 7.45-7.25(6H, m), 7.12(1H, dd, J=8.4 Hz), 6.67(1H, d, J=d Hz), 4.39(1H, dd, J=8.4 Hz), 3.39(1H, dd,J=12.4 Hz), 3.21(1H, dd, J=12.4 Hz), 1.46(9H, s), MS(LC/MS) m/z observed 464.87, expected 465.12 [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,94446-97-6, its application will become more common.

Reference:
Patent; viDA Therapeutics Inc.; Cameron, Dale R.; (36 pag.)US9458192; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65973-52-6, 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 65973-52-6, name is Methyl 4,6-dichloronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

[00217] Step B; 4.6-Dichloronicotinic acid:[00218] To a solution of methyl 4,6-dichloronicotinate in a mixture of THF (400 ml), MeOH ( 100 ml) andH2O ( 100 ml) was added a solution of NaOH (10 g) in 40 ml H2O. The mixture was stirred for 40 min. at room temp. Then, the solvents were reduced and it was acidified with cone. HCl to a pH of about 2. It was extracted using a mixture of Et2O/EtOAc and the organic layer was dried with Na2SO4. The solvents were removed and the residue dried in vacuo to obtain the title compound as a white solid (12.3 g, 69%). Rf (CHCl3/MeOH 10:1) = 0.85. 1H-NMR (300 MHz, DMSO-D6): delta = 8.80 (s, 1H), 7.90 (s, 1H).

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 65973-52-6, Methyl 4,6-dichloronicotinate.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; WO2008/89459; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 5470-70-2, name is Methyl 6-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H9NO2

a) 6-methyl-3-pyridylcarbinol Following the procedure of Example 2(b), except substituting methyl 6-methylnicotinate for N-cyclopropylmethyl isobutyramide, the title compound was prepared as a yellow oil (4.32 g, 83percent). MS (ESI): 123.8 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 5470-70-2.

Reference:
Patent; Halbert, Stacie Marie; Michaud, Evelyne; Thompson, Scott Kevin; Veber, Daniel Frank; US2002/49316; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 78686-79-0, Adding some certain compound to certain chemical reactions, such as: 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate,molecular formula is C7H5BrClNO2, 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 78686-79-0.

INTERMEDIATE 31Methyl 2-chloro-5-methylnicotinate; To a solution of methyl 5-bromo-2-chloronicotinate (1.05g, 4.19mmol), K3PO4 (2.95g, 13.90mmol), methylboronic acid (0.32g, 5.26mmol) and tricyclohexylphosphine (0.11g, 0.39mmol) in toluene/water (16ml/0.8ml) under nitrogen atmosphere was added Pd(OAc)2 (0.04g, 0.18mmol). The mixture was heated at 1000C overnight under nitrogen atmosphere. The reaction mixture was then cooled to room temperature and concentrated in vacuum. Ethyl acetate was added to the residue and this organic layer was washed with water, brine, dried over MgSO4, filtered and the solvent evaporated under vacuum to yield the desired product as a yellow oil. Yield=87% LRMS: m/z 186 (M+1 )+ Retention time: 4.84min

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. 78686-79-0, Methyl 5-bromo-2-chloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2008/77639; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 93683-65-9, 6-Chloro-3-nitropicolinonitrile, 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, Quality Control of 6-Chloro-3-nitropicolinonitrile, blongs to pyridine-derivatives compound. Quality Control of 6-Chloro-3-nitropicolinonitrile

Reference Example 20 (0115) 3-Amino-6-chloropyridine-2-carbonitrile (0116) To a solution of 6-chloro-3-nitropyridine-2-carbonitrile (0.32 g and concentrated hydrochloric acid (1.2 mL) in ethanol (3.6 mL) was added iron powder (0.34 g) at room temperature, and the mixture was heated at reflux for 30 minutes. The reaction mixture was cooled to room temperature, and basified by addition of saturated aqueous sodium hydrogen carbonate solution. To the mixture was added ethyl acetate, and the resulting mixture was filtered through a Celite pad, and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.24 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,93683-65-9, 6-Chloro-3-nitropicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Shimizu, Kazuo; Miyagi, Takashi; Ohno, Kohsuke; Ueno, Yasunori; Onda, Yusuke; Suzuki, Hikaru; (35 pag.)US2016/289206; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10177-29-4, 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. 10177-29-4, name is 4-Chloronicotinic acid. A new synthetic method of this compound is introduced below.

A mixture of 4-chloronicotinatic acid (7.88 g, 50 mmol) in dichloromethane (100 ml) was added thionyl chloride (12.7 ml, 150 mmol) and DMF (3 drops), and the reaction was refluxed for 2 h. After the reaction was cooled to room temperature, the solvent and thionyl chloride was removed under reduced pressure. Then ethanol (80 ml) and Et3N (13.9 ml, 100 mmol) were added to the residue and the resulting mixture was stirred at room temperature overnight. The solution was diluted with water (80 ml), and extracted with dichloromethane (50 ml 2). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by flash column chromatography with petroleum ether/ethyl acetate (10:1) to provide 7.89 g (85%) of 6 as a colorless oil. 1H NMR (300 MHz, CDCl3) d 9.20(s, 1H), 8.82 (d,J 6.0 Hz, 1H), 8.08 (d, J 6.0 Hz, 1H), 4.48 (q, J 7.5 Hz, 2H),1.43 (t, J 7.5 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,10177-29-4, its application will become more common.

Reference:
Article; Zou, Qingan; Duan, Hongliang; Ning, Mengmeng; Liu, Jia; Feng, Ying; Zhang, Liming; Zhu, Junjie; Leng, Ying; Shen, Jianhua; European Journal of Medicinal Chemistry; vol. 82; (2014); p. 1 – 15;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64321-24-0 ,Some common heterocyclic compound, 64321-24-0, molecular formula is C6H6ClN3O, 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.

Example 140C 7-Chloro-pyrido[2,3-d]pyrimidin-4-ol A mixture of Example 140B (1 g, 5.8 mmol) in triethylorthoformate (30 mL) was refluxed for 6 h then cooled. Hexane (150 mL) was added and the solid formed was filtered and washed with water and hexane to yield 0.27 g of product (26%). MS: (DCI/NH3) m/z=182 (M+1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64321-24-0, its application will become more common.

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 B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 81719-53-1, 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 81719-53-1 as follows.

To 4-hydrazinocarbonylpiperidine-1-carboxylic acid tert-butyl ester (500 mg) were added 3,5-dichloropyridine-2-carboxylic acid (475 mg), 1-hydroxybenzotriazole (420 mg),1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide.hydrochloride (590 mg), triethylamine (575 muL) and chloroform (10 mL) and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography (chloroform:methanol)to give 4-[N’-(3,5-dichloropyridine-2-carbonyl)hydrazinocarbonyl]piperidine-1-carboxylic acid tert-butyl ester (525 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,81719-53-1, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5975-12-2 , The common heterocyclic compound, 5975-12-2, name is 2,4-Dichloro-3-nitropyridine, molecular formula is C5H2Cl2N2O2, 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.

b) Synthesis of 4-chloro-3-nitro-pyridin-2-ol 2,4-dichloro-3-nitro-pyridine (4.01 g, 20.8 mmol) and cesium acetate (8.0 g, 41.6 mmol) were dissolved in anhydrous N,N-dimethyl formamide (104 ml) under nitrogen atmosphere, and the reaction mixture was heated to 800 and stirred for 18 hours. The reaction mixture was cooled to room temperature the reaction was quenched by adding water. The organic layer was extracted with ethyl acetate, and the combined organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure to obtain pale-yellow solid (1.69 g, 47%). 1H-NMR (DMSO-d6, 300 MHz); delta=8.24 (d, J=5.7 Hz, 1H), 7.09 (d, J=5.7 Hz, 1H).

The synthetic route of 5975-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ahn, Sung Oh; Park, Chan Hee; Im, Jun Hwan; Lee, Soon Ok; Lee, Kyoung June; Cho, Seong Wook; Ko, Kwang Seok; Han, Sun Young; Lee, Won Il; US2011/28467; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem