Pyridine-derivatives

Reference of 106014-21-5, 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. 106014-21-5, name is Dimethyl 3-chloropyridine-2,5-dicarboxylate. A new synthetic method of this compound is introduced below.

To a solution of dimethyl 3-chloropyridine-2,5-dicarboxylate (1.0 g, 4.4 mmol) in THF(10 mL) and MeOH (20 mL) was added powdered calcium chloride (3.9 g, 35 mmol). The suspension was cooled to 00C and sodium borohydride (416 mg, 11.0 mmol) was added portionwise. The resulting mixture was stirred for 3 h at 00C and poured into ice-water (200 mL), and extracted with DCM (2 x 100 mL). The combined organic layers were dried (Na2SO4), filtered and the solvent was removed in vacuo to yield methyl 5-chloro-6- (hydroxymethyl)nicotinate which was used in the next step without further purification. GC/MS (m/z): 201.0

At the same time, in my other blogs, there are other synthetic methods of this type of compound,106014-21-5, Dimethyl 3-chloropyridine-2,5-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; JERINI AG; WO2009/36996; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 4684-94-0, 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.4684-94-0, name is 6-Chloropicolinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

To 500mL three-necked flask equipped with a thermometer, was added DMF (200ml), between sequentially added trifluoromethylphenol (0.26mol, 42.2g), potassium carbonate (0.266mol, 37.2g), 2-chloro-6-carboxy pyridine (0.2mol, 31.6g), cuprous chloride (1.0 g of), heated to 140 deg.] C, the reaction 6.0H, cooled to room temperature, the reaction solution was poured into 600ml of ice water, pH = 3 adjusted with concentrated brine, and the precipitated solid was pumped was filtered off, washed with water, dried to obtain a white solid, yield: 75%

The chemical industry reduces the impact on the environment during synthesis 4684-94-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chen Lei; (6 pag.)CN108530351; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69045-78-9, 2-Chloro-5-(trichloromethyl)pyridine, 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, Recommanded Product: 69045-78-9, blongs to pyridine-derivatives compound. Recommanded Product: 69045-78-9

Example 4 In a 3000 cc autoclave equipped with a magnetic stirrer, a 40% aqueous solution of methylamine (814 g), ethanol (312 g) and Raney nickel (35 g) were charged. Hydrogen gas was introduced into the autoclave to a pressure of 3 Kg/cm2. While keeping a temperature at 30 C. or lower and supplying the hydrogen gas, a 58.8% solution of 2-chloro-5-trichloromethylpyridine in toluene (589 g) was added over 40 minutes. After the addition of the solution of 2-chloro-5-trichloromethylpyridine, the internal temperature was gradually raised to 40 C. At the same temperature, the hydrogen gas was supplied till the absorption of hydrogen ceased. After completion of reaction, the autoclave was cooled to room temperature, and the catalyst was filtrated off from the reaction mixture. The filtrate was analyzed by high pressure liquid chromatography to find that a yield of 2-chloro-5-methylaminomethylpyridine was 76%.

The synthetic route of 69045-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Koei Chemical Co., Ltd.; US5424437; (1995); A;,
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

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

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

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

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

Reference of 182275-70-3 , The common heterocyclic compound, 182275-70-3, name is 2-Iodo-6-methoxypyridine, molecular formula is C6H6INO, 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.

The mixture of Preparation Ria (1.0 g, 6.51 mmol)), 2-iodo-6-methoxy-pyridine (2.35 g, 9.77 mmol, 1.5 eq.), copper(I)-iodide (125 mg, 0.65 mmol, 0.1 eq.), potassium-phosphatetribasic (2.76 g, 13 mmol, 2 eq.), (1R,2R)-(-)-1,2-diaminocyclohexane (74 mg, 0.65 mmol,0.1 eq.) in PDO (50 ml) was stirred under inert atmosphere for 4 hours at 100 C. The inorganics was filtered off and the filtrate was evaporated. The resulted residue was purified by flash chromatography (DCM).

The synthetic route of 182275-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; WEBER, Csaba; VASAS, Attila; MOLNAR, Balazs; KISS, Arpad; MACIAS, Alba; MURRAY, James Brooke; LEWKOWICZ, Elodie; GENESTE, Olivier; CHANRION, Maia; DEMARLES, Didier; (105 pag.)WO2017/212012; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6938-06-3, Adding some certain compound to certain chemical reactions, such as: 6938-06-3, name is Butyl nicotinate,molecular formula is C10H13NO2, 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 6938-06-3.

Single crystal of I was prepared by the slow diffusion of two solutions, FeSO4*(NH4)2SO4*6H2O (0.106 mmol, 41.9 mg), ascorbic acid (0.104 mmol, 20.9 mg), and K[Au(CN)2] (0.200 mmol, 58.2 mg) in 10 mL of water using a small vial. The small vial was placed in a large vial, where the butyl nicotinate reacts with the mother solution through vapor diffusion.

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. 6938-06-3, Butyl nicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ueno, Shoutaro; Kawasaki, Takeshi; Kitazawa, Takafumi; Okabayashi, Jun; Bulletin of the Chemical Society of Japan; vol. 88; 4; (2015); p. 551 – 553;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem