Tag: M.W:100-200

Synthetic Route of 483324-01-2 , The common heterocyclic compound, 483324-01-2, name is 2-Chloro-4-(pyridin-3-yl)pyrimidine, molecular formula is C9H6ClN3, 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.

A 250 ml reactor, equipped with a mechanical stirrer and a reflux condenser, was charged with 2-chloro-4-(3-pyridyl)-pyrimidine (0.5 g, 2.6 mmol), 2-amino-4-nitrotoluene (0.5 g, 3.2 mmol), n-butanol (15 ml) and concentrated HCl (5 drops) and the mixture was refluxed for 38 hours. Then, the mixture was cooled, and 6 N NaOH was added to pH 8. The solvent was evaporated under reduced pressure and water (20 ml) was added to the residue, followed by extraction with dichloromethane (2×20 ml). The combined organic phase was concentrated to dryness to give the crude N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-pyrimidine-amine, which was purified by column chromatography to yield a product having 80% purity. The residue was re-slurried twice in methanol (2×2 ml) and in water (3 ml) and dried under reduced pressure

The synthetic route of 483324-01-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anli, Huang; Xing, Liu; Zelikovitch, Lior; Kaspi, Joseph; US2006/149061; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83640-36-2, 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 83640-36-2, name is 6-(Chloromethyl)nicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A. Preparation of 6-((8-bromo-7-(4-chlorophenyl)-5-methyl-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-2(3H)-yl)methyl)nicotinonitrile To a stirring solution of 8-bromo-7-(4-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (40 mg, 0.11 mmol) in DMF (0.25 mL) at room temperature under argon was added K2CO3 (50 mg, 0.36 mmol), followed by 6-(chloromethyl)nicotinonitrile (20 mg, 0.13 mmol). The reaction mixture was stirred at 70 C. for 1 h. The reaction mixture was cooled to room temperature, water (2 mL) and EtOAc (5 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure to obtain 55 mg of the title compound as a yellow solid. HPLC/MS: retention time=3.55 min, [M+H]+=454.

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 83640-36-2, 6-(Chloromethyl)nicotinonitrile.

Reference:
Patent; Sun, Chongqing; Sher, Philip M.; Wu, Gang; Ewing, William R.; Huang, Yanting; Lee, Taekyu; Murugesan, Natesan; Sulsky, Richard B.; US2007/4772; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 36357-38-7, 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. 36357-38-7, name is 5-Acetyl-2-methylpyridine. A new synthetic method of this compound is introduced below.

Sodium borohydride (2.3 g, 0.06 mol) was added in small portions over 30 mm, to a solution of compound 1(16.4 g, 0.121 mol) in ethanol (160 ml) at 0C and the reactionmixture was stirred at same temperature. After 1 h, the reaction mixture was diluted with sodium bicarbonate solution (sat) (2×200 ml) and extracted with dichloromethane (2×500 ml). The combined organic extract was dried over anhydrous sodium sulphate and concentrated to afford a pale yellow oil, which was purified by flash column chromatography (5% methanol/dichloromethane) to afford compound 11(17.0 g; 93% yield over 2 steps) as a pale yellow oil.ES-MS [M+1]+: 138.11H NMR (400 MHz, CDCI3): 68.35 (d, J = 2.0 Hz, 1H), 7.63 (dd, J = 8.0, 2.4 Hz, 1H),7.12 (d, J = 8.0 Hz, 1H), 4.89 (q, J = 6.5 Hz, 1H), 3.30 (brs, 1H), 2.50 (s, 3H), 1.48 (d, J = 6.5 Hz, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36357-38-7, 5-Acetyl-2-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; MINORYX THERAPEUTICS S.L.; GARCIA COLLAZO, Ana Maria; ECKLAND, David John Augustus; PIZCUETA LALANZA, Maria Pilar; MARTINELL PEDEMONTE, Marc; WO2015/150476; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 61494-55-1, 2-(2-Chloropyridin-3-yl)acetic 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, Application In Synthesis of 2-(2-Chloropyridin-3-yl)acetic acid, blongs to pyridine-derivatives compound. Application In Synthesis of 2-(2-Chloropyridin-3-yl)acetic acid

Example 9; 1-[4-(1H-benzimidazol-2-yloxy)phenyl]-3,3-dimethyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one dihydrochloride 9a) 1-[4-(benzyloxy)phenyl]-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one A mixture of 4-(benzyloxy)aniline hydrochloride (2.21 g), 4-methylbenzenesulfonic acid hydrate (0.178 g), and (2-chloropyridin-3-yl)acetic acid (Journal of Medicinal Chemistry, 1990, 33, 2697-2706.) (1.61 g) in 1-pentanol (15 mL) was stirred at 140 C. for 24 h. After cooling to room temperature, the mixture was added to SiO2, and the mixture was concentrated and purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane) to give 1-[4-(benzyloxy)phenyl]-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (1.39 g) as a pale yellow solid.MS (ESI+): [M+H]+317.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; TANIGUCHI, Takahiko; YOSHIKAWA, Masato; MIURA, Kasei; HASUI, Tomoaki; HONDA, Eiji; IMAMURA, Keisuke; KAMATA, Makoto; KAMISAKI, Haruhi; QUINN, John F.; RAKER, Joseph; CAMARA, Fatoumata; WANG, Yi; US2011/319394; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22620-27-5, 5-Chloronicotinic 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, Recommanded Product: 22620-27-5, blongs to pyridine-derivatives compound. Recommanded Product: 22620-27-5

EXAMPLE 7; 2-Amino-4-(5-chloro-pyridin-3-yl)-3-cyano-7-methyl-4H-pyrrolo[2,3-h]chromene; a) 5-Chloro-pyridine-3-carbaldehyde:; To a solution of oxalyl chloride (2.0 M solution in CH2Cl2, 30.0 mL, 60.0 mmol) in anhydrous CH2Cl2 (20.0 mL) cooled at 0 C., was added anhydrous DMF (3.0 mL, 38 mmol) dropwise, resulting in a white precipitate. The ice bath was removed and the white suspension was allowed to warm to room temperature. The white precipitate was filtered and collected on a sintered glass funnel. To a suspension of the above white precipitate (0.487 g, 3.81 mmol) in anhydrous acetonitrile (5.86 mL) and anhydrous THF (11.91 mL) at -55 C. was added pyridine (0.043 mL, 0.53 mmol) and 5-chloronicotinic acid (0.200 g, 1.27 mmol). The white suspension was warmed to room temperature over the next 3 h and then cooled to -78 C. While maintaining the internal temperature below -70 C., CuI (0.010 g) was added followed by the dropwise addition of LiAlH(t-BuO)3 (1.0 M solution in THF, 0.646 g, 2.54 mmol). The internal temperature was maintained below -70 C. for an additional 0.5 h and then the reaction was quenched with 2.0 N HCl (3 mL). The suspension was warmed to room temperature and diluted with ethyl acetate (150 mL), dried over Na2SO4, filtered through sintered glass and concentrated to a brown residue. The residue was purified by column chromatography (elution with EtOAC:hexanes, 1:4), and yielded 0.0484 g (27%) of the title compound as a white solid. 1H NMR (CDCl3): 10.11 (s, 1H), 8.95 (d, J=1.93 Hz, 1H), 8.81 (d, J=2.47 Hz, 1H), 8.15 (dd, J=2.47, 1.93 Hz, 1H).

The synthetic route of 22620-27-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cytovia, Inc.; US2006/104998; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 50501-38-7, 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 50501-38-7, name is 6-(Hydroxymethyl)picolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

The product of the previous step and N,N’-dicyclohexylcarbodiimide (19.3 g, 93.0 mmol) were added to a mixture of DMSO (22 ml) anhydrous H3PO4 (1.4 g) and the reaction was left to stir 1.5 hours. The reaction was filtered and washed with diethyl ether (2 x 30 ml) and water (2 x 30 ml). The reaction layers was separated and the organic layer was washed with saturated brine (2 x 30 ml), dried with MgS04, filtered and evaporated to yield (iib) as a yellow solid which was taken towards the next step without purification.

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 50501-38-7, 6-(Hydroxymethyl)picolinonitrile.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2006/21801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88912-24-7, 5,6-Dichloropicolinic 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, Recommanded Product: 5,6-Dichloropicolinic acid, blongs to pyridine-derivatives compound. Recommanded Product: 5,6-Dichloropicolinic acid

To a 100 ml round bottom flask equipped with a magnetic stirrer, reflux condenser and a nitrogen inlet were added 5,6-dichioropicolinic acid (5.00 g, 23.1 mmol), TEA (8.3 g, 81.0 mmol), ACN (39.9 g) and water (15.3 g). The solution was sparged for 30 mm with nitrogen (1 mE/mm) After sparging, 1,1 ?-bis(diphenylphosphino)ferrocene (dppf; 0.19 g, 0.343 mmol) and palladium(II) acetate (0.08 g, 0.356 mmol) were added to the solution. (4-Chioro-2-fluoro-3- methoxyphenyl)boronic acid 5.4 g, 26.9 mmol) was added in one portion, and heating was initiated. The reaction mixture was heated to 550 C., and was sampled and analyzed periodically by liquid chromatography. No boronic acid was remaining after 22 hours, and heating was stopped. The reaction mixture was allowed to cool to 45 C. Once at temperature, 50% sulfuric acid (7.2 g) was added. No precipitation was observed, so the mixture was cooled. A precipitate formed, which was isolated by filtration. The flask was rinsed with cold mother liquor to isolate all of the product. The wetcake was then rinsed with cold ACN- water solution (8.75 g and 11.25 g, respectively). The palladium content was analyzed in the wetcake, wash and mother liquors, with 96% of the palladium in the mother liquor and wash, and 4% in the wet cake. 98% of the total palladium added was recovered.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88912-24-7, 5,6-Dichloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Dow AgroSciences LLC; Biswas, Sanjib; Chakrabarti, Reetam; Huffman, Lauren M.; Leng, Ronald B.; Schuitman, Abraham D.; Spiers, Karin; Stottlemyer, Alan L.; Epp, Jeffrey B.; (18 pag.)US2016/340311; (2016); 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 81565-19-7, name is 3-Chloro-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 3-Chloro-4-(trifluoromethyl)pyridine

Step A. 3-Chloro-4-(trifluoromethyl)pyridine 1-oxide A mixture of 3-chloro-4-(trifluoromethyl)pyridine (2.00 g, 11.0 mmol) and H2O2 (3.2 mL, 31 mmol) in AcOH (6 mL) was stirred at 80 C. overnight. The reaction mixture was allowed to cool to ambient temperature and quenched with NaHSO3 solution. The mixture was concentrated under reduced pressure and the residue was added saturated NaHCO3 solution (30 mL). The resulting mixture was extracted with DCM (3 times). The combined organic phases were washed with aq. NaHCO3, water and brine, dried over Na2SO4 and concentrated under reduced pressure to give 2.11 g (97% yield) of the sub-title compound as a pink solid. LCMS calc. for C6H4ClF3NO (M+H)+: m/z=198.0. found: 198.0.

With the rapid development of chemical substances, we look forward to future research findings about 81565-19-7.

Reference:
Patent; INCYTE CORPORATION; Li, Yun-Long; Burns, David M.; Feng, Hao; Huang, Taisheng; Mei, Song; Pan, Jun; Vechorkin, Oleg; Ye, Hai-Fen; Zhu, Wenyu; Rafalski, Maria; Wang, Anlai; Xue, Chu-Biao; US2015/57265; (2015); 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 3430-22-6, name is 3-Bromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 3430-22-6

EXAMPLE 5 STR14 3-Bromoisonicotinic acid: 12.9 g (75 mmole) of 3-bromo-4-picoline was added to a purple solution of 23.7 g (0.15 mole) of potassium permanganate in 600 mL of water. This mixture was vigorously stirred 36 hrs. at 45 C. The resulting black solid was filtered and washed with 4*50 mL of hot water. The filtrate was concentrated to ~50 mL. A viscous liquid with black solid resulted. This was filtered through celite, which was washed with 3*20 mL of water. 150 mL of ice cold 2N hydrochloric acid was added. The resulting voluminous white precipitate was filtered and the solid was dried in vacuo to give 3-bromoisonicotinic acid as white powder. 1 H NMR (D6 -DMSO, 400 MHz): delta8.84 (s; H2); 8.63 (d; J=5 Hz; H6); 7.66 (d; J=5 Hz; H5)

With the rapid development of chemical substances, we look forward to future research findings about 3430-22-6.

Reference:
Patent; Merck & Co. Inc.; US5294610; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 127356-38-1, 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. 127356-38-1, name is 2-Methoxy-5-nitropyridin-4-amine, molecular formula is C6H7N3O3, 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.

Aq. conc. HCl (1 ml, 32.9 mmol) was diluted with water. To the solution was added tin (II) chloride (0.448 g, 2.365 mmol), followed by 2-methoxy-5-nitropyridin-4-amine (0.1 g, 0.591 mmol). The mixture was heated to 60 C. for 18 h. The reaction mixture was cooled to room temperature, then basified using 10% NaOH solution. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude compound was triturated with 10% ethyl acetate in Pet-ether to afford 6-methoxypyridine-3,4-diamine (0.06 g, 0.366 mmol, 62.0% yield) as a solid. 1H NMR (400 MHz, DMSO-d6): delta ppm 7.21 (s, 1H), 5.83 (s, 1H), 5.39 (b s, 2H), 4.04 (b s, 2H), 3.62 (s, 3H).

According to the analysis of related databases, 127356-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; Sun, Li-Qiang; Zhao, Qian; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Gillis, Eric P.; Scola, Paul Michael; (81 pag.)US9643999; (2017); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem