Tag: M.W:100-200

Reference of 59290-81-2, Adding some certain compound to certain chemical reactions, such as: 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid,molecular formula is C7H6N2O4, 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 59290-81-2.

Compound D5 (208g, 1.15mol) was dissolved in t-butanol (2.1L), and thereto were added DPPA (37OmL) and TEA (223mL). The mixture was heated under reflux overnight, quenched by the addition of brine (10OmL). The resulting mixture was extracted by EA (1.0L) for three times. The combined organic phase was washed with brine (10OmL), dried over anhydrous MgSO4 and concentrated under vacuo. The residue was purified by column chromatography (EA : PE=I :2) to provide compound D6 (1 14.5g, 40% yield) as yellow solid. IH NMR (CDC13, 300MHz): delta=l .54 (s, 9H), 2.60 (s, 3H), 6.53 (s, IH), 8.98-8.99 (d, IH), 9.09-9.10 (d, IH). LC-MS [M+l] +: 252.0.

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. 59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 20511-15-3 ,Some common heterocyclic compound, 20511-15-3, molecular formula is C5H5ClN2, 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 48% aqueous tetrafluoroboric acid solution (10 ml) was added to a solution of 4-chloropyridin-3-amine (1.29 g, 10.0 mmol) in ethanol (10 ml) at 0C. A solution of sodium nitrite (725 mg, 10.5 mmol) in water (10 ml) was added to the resultant mixed solution at the same temperature, and it was stirred at the same temperature for 30 minutes. The precipitate was collected by filtration and washed with ethanol, and the resultant brown solid (1.94 g) was then dissolved in acetonitrile (10 ml). A mixed solution of sodium cyanide (980 mg, 20.0 mmol) and copper(I) cyanide (896 mg, 10.0 mmol) in water (10 ml) and acetonitrile (1 ml) was added to the resultant solution at 0C, and it was stirred while gradually warming to room temperature for 10 hours. The reaction mixture was cooled to 0C, after which a saturated aqueous solution of sodium bicarbonate was added, and it was stirred for five minutes. The resultant solution was extracted with ethyl acetate, and the organic layer was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (605 mg, 44%) as a pale yellow solid. 1H-NMR (300 MHz, CDCl3) delta: 8.87 (1H, s), 8.72 (1H, d, J = 3.9 Hz), 7.51 (1H, d, J = 3.9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20511-15-3, its application will become more common.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; MURATA, Takeshi; KAWADA, Hatsuo; NIIZUMA, Satoshi; HARA, Sousuke; HADA, Kihito; SHIMADA, Hideaki; TANAKA, Hiroshi; MIO, Toshiyuki; EP2842946; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. A new synthetic method of this compound is introduced below.

2-(6-chloro-3-pyridyl)methyl-1,4,5,6-tetrahydropyrimidine [Compound 8] To a stirred solution of 20 ml of toluene were added 3.75 ml of 1M trimethylaluminum/hexane solution and 315 mul (3.77 mmol) of trimethylenediamine under argon atmosphere at room temperature, and to this mixture was further added 500 mg (2.5 mmol) of ethyl (6-chloro-3-pyridyl)acetate in toluene solution. The mixture was stirred for 22 hours at 100 C. under refluxing. After cooling the reaction mixture to room temperature, 5 ml of chloroform, 5 ml of methanol and 1 ml of water were added. Then precipitated gel was removed off by filtration and washed with a mixture of chloroform and methanol (9:1), and the filtrate was concentrated under reduced pressure. The resulting residue was purified by aminopropyl-coated silica gel (Chromatorex NH-type; Fuji Silysia Chemical Ltd.) column chromatography (eluent; dichloromethane:ethyl acetate=30:1, then dichloromethane_methanol=50:1) to give 442 mg (yield; 84.4%) of 2-(6-chloro-3-pyridyl)methyl-1,4,5,6-tetrahydropyrimidine as crystalline. This product was dissolved in methanol and to this solution was added 245 mg (2.11 mmol) of fumaric acid, and the mixture was concentrated under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,197376-47-9, its application will become more common.

Reference:
Patent; Imoto, Masahiro; Iwanami, Tatsuya; Akabane, Minako; Tani, Yoshihiro; US2003/100769; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1074-98-2 ,Some common heterocyclic compound, 1074-98-2, molecular formula is C6H6N2O3, 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-Methyl-4-nitro-pyridine-N-oxide (5.34 g, 34.7 mmol, 1 equiv.) and N,N-dimethylformamide diethyl acetal (10.5 mL, 61.4 mmol, 1.8 equiv.) were combined in 50 mL anhydrous DMF and heated to 120 C. for 3 h. The reaction was allowed to cool back to room temperature and the DMF solvent was removed in vacuo. The residue was treated with ~80 mL toluene, which was then removed in vacuo as well. Finally the residue was mixed with benzene and filtered. The desired vinyl amine was obtained as a dark purple solid (6.74 g, 32.2 mmol, 93%), which was used as is in the next step. The vinyl amine from above (3.37 g, 16.1 mmol, 1 equiv.) and 1.75 mL of water were mixed in 50 mL EtOH. Ammonium formate (4.56 g, 72.5 mmol) and 10% palladium-on-carbon (600 mg) were added and the mixture was heated to a gentle reflux for 1 h. TLC and MS (ES+) revealed no starting material but showed the presence of two major components, the desired 5-aza-indole and its N-oxide. The reaction was left stirring for a further 2 h after more ammonium formate and more palladium catalyst were added. Finally the reaction was cooled to room temperature, filtered and solvents removed in vacuo. 5% NaOH aqueous solution was added and the mixture was extracted with EtOAc. The combined organics were dried (MgSO4), filtered, and the solvent was removed in vacuo, providing 0.555 g of desired 5-aza-indole (4.70 mmol, 29% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1074-98-2, its application will become more common.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2003/162968; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58327-75-6, 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. 58327-75-6, name is 3-Aminothieno[2,3-b]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2S, 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.

A solution of 238 (17 g, 87 mmoi) in phosphoc acid (150 mL, 85% aqueous solution) is stirred at 100 C for 45 minutes. Saturated aqueous sodium bicarbonate solution is then added at room temperature to adjust to pH 8. The solid is collected by filtration and washed with EtOH (100 mL x 2) to give US as an orange solid (9.0 g, 54% yield). (MS:[M+H] 152.1)

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 58327-75-6, 3-Aminothieno[2,3-b]pyridine-2-carboxylic acid.

Reference:
Patent; IMMUNE SENSOR, LLC; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHONG, Boyu; SUN, Lijun; SHI, Heping; LI, Jing; CHEN, Chuo; CHEN, Zhijian; (270 pag.)WO2017/176812; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 23056-40-8, 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. 23056-40-8, name is 2-Chloro-5-methyl-3-nitropyridine, molecular formula is C6H5ClN2O2, 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 mixture of 4 (1.0 g, 6.5 mmol) and c-H2SO4 (27 mL), sodium dichromate (2.5 g) was added slowly. After stirring at rt for 15 h, the mixture was slowly added into cracked ice. The mixture was extracted with EtOAC. The organic extract was washed with brine, dried over Na2SO4, and evaporated in vacuo to provide product 5 as a green solid (1.0 g, 85%). 1H NMR (300 MHz, DMSO-d6) delta: 13.32 (s, 1H), 8.64 (d, J = 2.4 Hz, 1H), 8.37 (d, J = 2.4 Hz, 1H).

According to the analysis of related databases, 23056-40-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Chao; Yang, Su Hui; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kyung-Tae; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 985 – 995;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92992-85-3, 2-Bromo-3,5-dimethylpyridine, 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, 92992-85-3, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-3,5-dimethylpyridine

To 2-bromo-3,5-dimethylpyridine (10.26 g) were added (S)-1-(tert-butoxycarbonyl)-3-aminopyrrolidine (10.27 g),tris(dibenzylideneacetone)dipalladium(0)(505 mg),2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1 g),sodium tert-butoxide (7.24 g) and toluene (180 mL) and the mixture was stirred at 80c for 3 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by column chromatography (hexane:ethyl acetate). The solvent was evaporated,ethyl acetate (50 mL),4N hydrogen chloride/1,4-dioxane solution (50 mL) and methanol (10 mL) were added to the obtained residue,and the mixture was stirred at room temperature for 2.5 hr. To the reaction mixture was added diethyl ether,and the supernatant was removed by decantation. To the obtained residue was added ethyl acetate/ethanol,and the precipitate was collected by filtration to give the title compound (11.9 g). MS(ESI)m/z:192(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,92992-85-3, 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

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 77618-99-6, name is 2-Amino-5-(methylthio)pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Amino-5-(methylthio)pyridine

Step 2: 4-Chloro-7-[5-(methylthio)-2-pyridinyl]-6,7-dihydro-5H-pyrrolo[2,3- cflpyrimidine (200)To a stirred solution of (4,6-dichloro-5-pyrimidinyl)acetaldehyde 209 (see example 116, step 1 , 3.41 g, 17.8 mmol) in MeOH (180 mL) was added 199 (3.0 g, 21.4 mmol) at RT. The reaction mixture was cooled to -15 0C with an ice/methanol bath and glacial acetic acid (3.1 mL, 53.4 mmol) and NaBH3CN (3.35 g, 53.4 mmol) were added. The reaction mixture was stirred at -15 0C for 15 min then allowed to warm to RT and stir for 19 h. The reaction mixture was then diluted with water (50 mL) and extracted with CH2CI2 (3 x 100 mL). The combined organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a yellow oil. The crude oil was dissolved in THF (500 mL) with stirring and then f-BuOK (5.99 g, 53.4 mmol) was added in one portion at RT. The reaction mixture changed immediately to a brown color and was stirred at RT for 22 h. The reaction mixture was quenched with water (50 mL), concentrated under reduced pressure, and then redissolved in EtOAc (200 mL). The organic layer was washed with water (1 x 50 mL) and the aqueous layer was extracted with EtOAc (2 x 100 ml_). The combined organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a brown oil. The crude oil was purified using SiO2 flash chromatography (20% to 40% EtOAc in hexanes; monitored at 319 nm) to give 550 mg (1 1%) of the title product 200 as a colorless oil. 1H NMR (400 MHz, CDCI3): delta 8.57 (d, J = 9.0 Hz, 1 H), 8.43 (s, 1 H), 8.29 (d, J = 2.4 Hz, 1 H), 7.68 and 7.66 (dd, J1 = 8.8 Hz, J2 = 2.4 Hz, 1 H), 4.37 – 4.33 (m, 2 H), 3.16 (t, J = 8.8 Hz, 2 H), 2.47 (s, 3 H).

With the rapid development of chemical substances, we look forward to future research findings about 77618-99-6.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 81803-60-3 ,Some common heterocyclic compound, 81803-60-3, molecular formula is C10H10N2O2, 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.

To an ice cold solution of ethyl imidazo[l,5-alpha]pyridine-3-carboxylate (10 g, 52.6 mmol) in acetonitrile (500 mL) was added N-bromo succinimide (9.36 g, 52.6 mmol). The mixture was allowed to stir for 1 h at which time triethylamine (10 mL) was added to the deep red- violet solution. The color dissipated and the solution was concentrated. Purification of the crude solid by silica gel chromatography (0-20% EtOAc/Hexanes) provided a white crystalline solid (13.5 g 95%). MS 268.9 (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,81803-60-3, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2008/85302; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 298709-29-2, 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.298709-29-2, name is 3,5-Difluoropicolinonitrile, molecular formula is C6H2F2N2, molecular weight is 140.0903, as common compound, the synthetic route is as follows.

A solution of methylmagnesium bromide (36.8 ml, 117.78 mmol) in THF (50ml) was stirred under N2 and cooled to -78C. 3,5-Difluoropicolinonitrile (15.0 g, 107.07 mmol) in THF (50 ml) was added drop wise with an addition funnel at such a rate that the internal temperature was kept below -4C. After the addition was complete, the reaction mixture was poured into a IM HCl (100 ml, chilled in an ice bath). The reaction mixture was stirred at 00C for 30 minutes and room temperature for 30 minutes. To this solution 150 ml of EtOAc was added to extract product. The aqueous phase was neutralized to pH 9 with NaHCO3 and extracted with EtOAc (2 X 20 ml). The organic layers were combined and the volatiles were removed under reduced pressure. Purification by ISCO (0-10% EtOAc- hexanes) gave the title product as light yellow oil. LCMS: 158 [M+H]

The chemical industry reduces the impact on the environment during synthesis 298709-29-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/150462; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem