Category: pyridine-derivatives

Electric Literature of 98121-41-6, 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. 98121-41-6, name is 3-Amino-5,6-dichloropyridine, molecular formula is C5H4Cl2N2, 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 5,6-dichloro-pyridin-3-ylamine (40.0 g, 0.245 mol, 1.0 equiv.) in dichloromethane (300 mL) at 0 C was added boron trifluoride diethyl etherate (42.0 g, 0.296 mol, 1.2 equiv.) followed by 2-methyl-2-nitrosooxy-propane (38.0 g, 0.369 mol, 1.5 equiv.). The resulting reaction was allowed to warm to 25 C. The slurry of the product was stirred at this temperature for 30-60 min and filtered to afford 5,6-dichloro-pyridine-3-diazonium tetrafluoroborate (51.0 g, 0.195 mol).5,6-Dichloro-pyridine-3-diazonium tetrafluoroborate (180 g, 0.688 mol, 1.0 equiv.) was dissolved in Ac2O (540 mL) and stirred at RT for a few minutes. Then, the mixture was heated to 60 C. Acetic acid 5,6-dichloro-pyridin-3-yl ester was detected by LCMS. The acetic acid was evaporated, the precipitate was diluted with DCM and evaporated in vacuo. The mixture was purified on silica gel (1% EtOAc in petroleum ether as eluent) to afford acetic acid 5,6-dichloro-pyridin-3-yl ester (84.0 g, 0.408 mol).

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 98121-41-6, 3-Amino-5,6-dichloropyridine.

Reference:
Article; Duplessis, Martin; Morency, Louis; James, Clint; Minville, Joannie; Deroy, Patrick; Morin, Sebastien; Thavonekham, Bounkham; Tremblay, Martin; Halmos, Ted; Simoneau, Bruno; Bousquet, Yves; Sturino, Claudio; Tetrahedron Letters; vol. 54; 19; (2013); p. 2303 – 2307;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2789-25-5, 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 2789-25-5, name is 2-Chloro-3-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

3c) 4-amino-2-hydroxy-3-nitropyridine A solution of 18.0 g (104 mmol) of 4-amino-2-chloro-3-nitropyridine in 120 ml dimethylsulphoxide and 30 ml of water was stirred for four hours at 130 C. The solution was then cooled and left to stand overnight while cooling with ice. The product that crystallized out was suction filtered, washed with a little water and dried at 50 C. Yield: 69% of theory. C5H5N3O3 (155.11) Mass spectrum: (M+H)+=156 (M-H)-=154

According to the analysis of related databases, 2789-25-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim Pharma GmbH Co. KG; US2005/20574; (2005); 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.4966-90-9, name is 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one, molecular formula is C6H6N2O4, molecular weight is 170.12, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Part A A mixture of 6-methyl-3-nitropyridine-2,4-diol (50 g, 0.29 mol) and phosphorus oxychloride (500 mL) was heated at 90 C. overnight. The excess phosphorus oxychloride was removed under reduced pressure. The resulting black oil was poured into water (1.8 L) and ice. This mixture was extracted with chloroform (*8, 3L total) and filtered to remove black particulates and break up an emulsion. The combined organics were washed with 10% sodium carbonate (*2) and brine, dried and then concentrated under reduced pressure to provide 52 g of an amber oil. This oil was recrystallized from heptane (115 mL) to provide 43.5 g of 2,4-dichloro-6-methyl-3-nitropyridine as large amber crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4966-90-9, 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; 3M Innovative Properties Company; US6545016; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109880-43-5, 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.109880-43-5, name is Methyl 4-chloro-6-(hydroxymethyl)picolinate, molecular formula is C8H8ClNO3, molecular weight is 201.61, as common compound, the synthetic route is as follows.

1.5 g of compound 13 (7.4 mmol, 1 eq.) are dissolved in 200 mE dichloromethane and 3 mE triethylaminc are added (22.2 mmol, 3 eq.). Then 0.87 mE of mesyl chloride is added (11.1 mmol, 1.5 eq.) slowly and a progressive yellow coloring of the mixture is observed. The reaction progress is followed by CCM and stopped after 30 mm. 100 mE of a saturated solution of NaHCO4 are added and the organic phase is washed with water (up to pH=7) and brine. The organic solution is then dried on Na2SO4 and evaporated to give 2 g of a yellow oil of compound 14 used without thrther purification (quantitative yield). ?H-NMR (300 MHz, CDC13) oe (ppm)=8.1 (s, 1H),7.68 (s, 1H), 5.40 (s, 2H), 4.01 (s, 3H), 3.17 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 109880-43-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ECOLE NORMALE SUPERIEURE DE LYON; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE CLAUDE BERNARD LYON I; COMMISSARIAT A L’ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; MAURY, Oliver; GIRARD, Eric; ENGILBERGE, Sylvain; RIOBE, Francois; (76 pag.)US2018/362550; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16744-81-3, Adding some certain compound to certain chemical reactions, such as: 16744-81-3, name is 4-Methoxypicolinaldehyde,molecular formula is C7H7NO2, 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 16744-81-3.

Examples; Final products; 1. (R. S)-2- [3-F4-METHOXYPYRIDIN-2-Y)) PROP-2-Y .]-3H-IMIDAZO [4. 5-B] PYRIDINE HYDROCHTORIDE; A solution of 0.59 g of 4METHOXYPYRIDINE-2-CARBALDEHYDE (Ashimori et al., Chem. Pharm. Bull. 38,2446- 2458 (1990) ) in 19 ml of methanol is treated with 1.9 g of {1- (3H-imidazo [4,5-b] pyridin-2-yl)-ethyl}- triphenyl-phosphonium chloride (compound A1). 3.3 ml of a solution of sodium methanolate in methanol (1.3 M) are added dropwise at 50° C. The reaction mixture is stirred at 50°C for 4 h and evaporated to dryness. The resulting residue is chomatographed on silica gel using DICHLOROMETHANE/METHANOL 20: 1 to give 1.75 g of a colorless, amorpheous solid, which is dissolved in 190 ml of methanol. 1.5 ml of glacial acetic acid and 388 mg of palladium on active carbon (10percent Pd) are added and the suspension is stirred at room temperature for 2.5 d under hydrogen atmosphere. Then the catalyst is filtered off and the reaction mixture is concentrated to dryness. After CHROMATOGRAPHICAL purification of the residue on silica gel (DICHOROMETHANE/METHANOL 25: 1) and evaporation of the eluents, 837 mg of an oil are obtained, which is dissolved in 160 ml of DICHLOROMETHANE. 2 ml of an ethereal hydrochloric acid solution (2.0 M) are added to the solution under ice-cooling. After LYOPHILLIZATION from dioxane, 0.951 g of the title compound are obtained as a colorless LYOPHILISATE. M. p. 61 °-64°C. MS: 269.1 (MH+). TLC: Rf = 0.44 (dichloromethane/methanol 10: 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. 16744-81-3, 4-Methoxypicolinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALTANA PHARMA AG; WO2005/30768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15862-50-7, 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. 15862-50-7, name is 3-Bromo-2-methoxy-5-nitropyridine. A new synthetic method of this compound is introduced below.

Step 2 Scheme 38:a bTo a solution of a ( 6.8 g , 29 mmol ) in 78 mL of EtOH and l OmL of H20 was added 0.8 mL of cone. HC1 and iron powder ( 49 g ,174 mmol ) with stirring. The resulting solution was heated at 80C under a nitrogen atmosphere for 3 hrs and cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated to afford b (5.1 g, 86%) as a brown-yellow residue, which was used directly to next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-50-7, 3-Bromo-2-methoxy-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENZYME CORPORATION; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; MAZITSCHEK, Ralph; CLARDY, Jon, C.; WIRTH, Dyann; WIEGAND, Roger; URGAONKAR, Sameer; BANIECKI, Mary, Lynn; CORTESE, Joseph; CELATKA, Cassandra; XIANG, Yibin; SKERLJ, Renato; BOURQUE, Elyse, M.j.; WO2011/53697; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 185315-53-1, Adding some certain compound to certain chemical reactions, such as: 185315-53-1, name is 3-Chloro-2-(chloromethyl)pyridine,molecular formula is C6H5Cl2N, 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 185315-53-1.

General procedure: A mixture of N-tert-butyl-7-(3,3-difluoropyrrolidin-l-yl)-3H-triazolo[4,5-d]pyrimidin-5- amine (25 mg, 0.08 mmol), NEt3 (14.6 mg, 0.144 mmol) and l-(bromomethyl)-2- (trifluoromethyl)benzene (26.8 mg, 0.112 mmol) in 2 mL DMF was stirred at room temperature for 5 h. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt . After evaporation of the product containing fractions 5.2 mg (14 %) of the title compound was isolated. MS(m/e): 456.4 (MH+). Example 78. N-[(3S)-l-[3-[(3-Chloropyridin-2-yl)methyl]-5-(2,2-dimethylpropoxy)triazolo[4,5- d]pyrimidin-7-yl]pyrrolidin-3-yl]acetamide; In analogy to the procedure described for the synthesis of N-tert-butyl-7-(3,3- difluoropyrrolidin-l-yl)-3-[[2-(trifluoromethyl)phenyl]methyl]triazolo[4,5-d]pyrimidm amine (example 22) the title compound was prepared from N-[(3S)-l-[5-(2,2- dimethylpropoxy)-3H-triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-yl]acetamide and 3- chloro-2-(chloromethyl)pyridine. MS(m/e): 459.4 (MH+).

According to the analysis of related databases, 185315-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ROEVER, Stephan; ROGERS-EVANS, Mark; NETTEKOVEN, Matthias; SCHMITT, Sebastien; GRETHER, Uwe; KIMBARA, Atsushi; WO2015/32769; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53636-68-3 , The common heterocyclic compound, 53636-68-3, name is 3-Amino-5-chloropicolinic acid, molecular formula is C6H5ClN2O2, 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.

Step 2;. Preparation of 3-Amino-5-chloro-pyridine-2-carboxylic acid methyl ester; Heat at 90 C a mixture of 5-chloro-3-nitro-pyridine-2-carbonitrile (1.0 g, 5.90 mmol) and tin (II) chloride (6.79 g, 29.5 mmol) in ethanol (10 mL) for 3 h. Evaporate the solvent under reduced pressure, add a solution of 35% hydrochloric acid (5 mL) and reflux the mixture for 6 h. Concentrate the reaction in vacuo to dryness and dissolve the resulting residue in methanol (20 mL). Add thionyl chloride (0.95 mL, 7.08 mmol) at room temperature and heat the mixture at 90 C for 24 h. Remove the solvent under reduced pressure, add ethyl acetate, and wash with a saturated solution of sodium bicarbonate. Separate the organic layer, dry over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue using silica gel chromatography, eluting with ethyl acetate to afford the title compound (0.77 g, 70%). H-NMR (CDCl3, 3 00 MHz): 8 3.97 (s, 3 H) ; 5.85 (bs, 2 H) ; 7.06 (d, J = 2.0 Hz, 1H), 7.97 (d, J = 2.0 Hz, 1H).

The synthetic route of 53636-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/97805; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 717843-51-1 ,Some common heterocyclic compound, 717843-51-1, molecular formula is C7H8BrNO, 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.

(3) Synthesis of 3-bromo-5-chloro-2-methoxy-4-methylpyridine 3-bromo-2-methoxy-4-methylpyridine (100 mg) was added to DMF (575 muL). NCS (72.5 mg) was added to the solution, and the mixture was stirred at 80 C. for three hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (100 mg). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.51 (s, 3H), 3.98 (s, 3H), 8.02 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,717843-51-1, its application will become more common.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (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.184416-84-0, name is 2,3-Dichloroisonicotinic acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.Application In Synthesis of 2,3-Dichloroisonicotinic acid

A mixture of 2,3-dichloroisonicotinic acid (960 mg, 5.00 mmol) and BH3 FontWeight=”Bold” FontSize=”10″ THF (1.0 M, 25 mL, 25 eq) was heated at 60 C for 4 h. After cooling to RT, MeOH (5 mL) was added, and the volatiles were removed under reduced pressure. The reaction mixture was diluted with water (50 mL) and extracted with DCM (50 mL x 3). The combined organic phase was washed with brine (100 mL), dried over Na2SC>4, filtered and concentrated to give (2,3- dichloropyridin-4-yl)methanol (400 mg, 45%) as a white solid. MS (ES+) C6H5C12N0 requires: 178, found: 179 [M+H]+. XH NMR (500 MHz, i-DMSO) delta 8.38 (d, J = 5 Hz, 1H), 7.58 (d, J= 5 Hz, 1H), 5.85-5.75 (br s, 1 H), 4.61 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,184416-84-0, 2,3-Dichloroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; TESARO, INC.; JONES, Philip; CZAKO, Barbara; BURKE, Jason P.; CROSS, Jason; LEONARD, Paul Graham; TREMBLAY, Martin; MANDAL, Pijus; (232 pag.)WO2018/119387; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem