Day: August 16, 2021

Related Products of 884494-81-9, 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.884494-81-9, name is 3-Bromo-5-fluoro-2-methoxypyridine, molecular formula is C6H5BrFNO, molecular weight is 206.01, as common compound, the synthetic route is as follows.

A solution 3-bromo-5-fluoro-2-methoxypyridine (4.00 g, 19.4 mmol), 2-(but-3-ynyl)isoindoline-1,3-dione (3.87 g, 19.4 mmol) and TEA (10.8 mL, 78 mmol) in DMF (40 mL) was degassed with argon. After addition of Pd(PPh3)4 (1.12 g, 0.971 mmol) and CuI (0.370 g, 1.94 mmol), the reaction mixture was heated at 90 C. for 2 hours and cooled to room temperature. After addition of MeOH, a precipitated solid was collected by filtration. The solid was washed with MeOH and dried under vacuum to afford 2-(4-(5-fluoro-2-methoxypyridin-3-yl)but-3-ynyl)isoindoline-1,3-dione (5.80 g, 92%) as a white fluffy solid. 1H-NMR (CDCl3, Varian, 400 MHz): delta 2.90 (2H, t, J=6.8 Hz), 3.85 (3H, s), 3.99 (2H, t, J=6.8 Hz), 7.34 (1H, dd, J=7.6, 2.4 Hz), 7.73-7.75 (2H, m), 7.87-7.89 (3H, m).

The chemical industry reduces the impact on the environment during synthesis 884494-81-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; HANDOK INC.; CMG Pharmaceutical Co., Ltd.; Kim, Moonsoo; Lee, Chaewoon; Lee, Gilnam; Yoon, Cheolhwan; Seo, Jeongbeob; Kim, Jay Hak; Lee, Minwoo; Jeong, Hankyul; Choi, Hyang; Jung, Myung Eun; Lee, Ki Nam; Kim, Hyun Jung; Kim, Hye Kyoung; Lee, Jae Il; Lee, MinWoo; Kim, Misoon; Choi, Soongyu; (124 pag.)US2016/168156; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 15871-85-9 , The common heterocyclic compound, 15871-85-9, name is 2-Methoxypyridine-5-carbonitrile, molecular formula is C7H6N2O, 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) 6-methoxynicotine acid To a solution of 6-methoxynicotinonitrile (5.00 g) in ethanol (100 mL) was added 2 M aqueous potassium hydroxide solution (20 mL). The reaction mixture was heated at reflex for 2 hr, and the solvent was evaporated under reduced pressure. To the residue was added water, the pH of the mixture was adjusted to 4-5 with 2 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (4.2 g). 1H NMR (400 MHz, DMSO-d6) delta 3.92 (3H, s), 6.86-6.92 (1H, m), 8.11-8.15 (1H, m), 8.73 (1H, d, J = 2.0 Hz), 13.0 (1H, s).

The synthetic route of 15871-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIKAMI, Satoshi; NAKAMURA, Shinji; ASHIZAWA, Tomoko; SASAKI, Shigekazu; TANIGUCHI, Takahiko; NOMURA, Izumi; KAWASAKI, Masanori; EP2848618; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 573675-25-9, 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. 573675-25-9, name is 5-Bromo-3-nitropicolinonitrile, molecular formula is C6H2BrN3O2, 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.

Step 3. 5-Broino-3-fluoropyridine-2-carbonitrile. Sulfuric acid (0.02 eq) was added to a solution of tetrabutylammonium fluoride (3 eq) inDMF (5 vol) and the mixture cooled to -40 0C. A solution of the compound of Step 2 (1 eq) in DMF (2 vol) was added maintaining the temperature < -35 0C. After about 20 minutes 2N HCl (3 vol) was added followed by IN HCl (15 vol). The precipitated product was collected by filtration to give the desired product. 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 573675-25-9, 5-Bromo-3-nitropicolinonitrile. Reference:
Patent; MERCK & CO., INC.; MERCK FROSST CANADA LTD.; WO2006/52514; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 62733-99-7, name is Methyl 3-hydroxypicolinate. A new synthetic method of this compound is introduced below., Safety of Methyl 3-hydroxypicolinate

To a solution of 3-hydroxy-pyridine-2-carboxylic acid methyl ester (200 mg, 1.3 mmol) in N,N-dimethylformamide (2.0 ml) was added at 22 C. sodium hydride (55% in oil, 64 mg) and stirring was continued until gas evolution ceased. The suspension was cooled to 0 C. and treated with trifluoroethyl trifluoromethanesulfonate (728 mg) and stirring was continued at 22 C. for 2 hours. The mixture was partitioned between saturated sodium hydrogen-carbonate solution and ethyl acetate, and the organic layer was dried and evaporated. The residue was purified by chromatography on silica using n-heptane and ethyl acetate (3:1) as the eluent to give 3-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester as a pale green oil. Mass (calculated) C9H8F3NO3 [235.16]; (found) [M+H]+=236.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 62733-99-7, Methyl 3-hydroxypicolinate.

Reference:
Patent; Andreini, Matteo; Banner, David; Guba, Wolfgang; Hilpert, Hans; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Power, Eoin; Roger-Evans, Mark; Travagli, Massimiliano; Valacchi, Michela; Woltering, Thomas; Wostl, Wolfgang; US2011/46122; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73870-24-3 ,Some common heterocyclic compound, 73870-24-3, molecular formula is C6H7Br2N, 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.

General procedure: Compounds 20-26 (1 equiv.) were dissolved in DMF followed by the addition of potassium carbonate (1 – 3 equiv.) and the corresponding benzyl- or pyridinylderivate (1-2 equiv.). This mixture was allowed to stir at various temperatures and timespans, all of which are further specified at the corresponding compounds reported below. The crude product was then purified by either normal phase or reversed phase flash chromatography to yield compounds 30-36 and 40-46. The exact conditions of these purifications are reported below for each compound individually.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73870-24-3, its application will become more common.

Reference:
Patent; VIB VZW; UNIVERSITEIT ANTWERPEN; UNIVERSITEIT GENT; VANDENABEELE, Peter; VANDEN BERGHE, Tom; AUGUSTYNS, Koen; HOFMANS, Sam; VAN DER VEKEN, Pieter; DEVISSCHER, Lars; (66 pag.)WO2019/154795; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1101120-05-1 , The common heterocyclic compound, 1101120-05-1, name is 3-Formylpyrazolo[1,5-a]pyridine-5-carbonitrile, molecular formula is C9H5N3O, 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.

General procedure: These were made using NaHCO3 or 2,6-lutidine as detailed below, unless otherwise stated. Methylhydrazine sulfate (1.2 equiv) and NaHCO3 (5 equiv) were added to a solution of 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile (2) (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The solvent was removed in vacuo and the residue taken up in CH2Cl2 and water. The layers were separated and the aqueous phase extracted with CH2Cl2, then the combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography or trituration then afforded the hydrazides. Alternatively, methylhydrazine sulfate (1.2 equiv) and 2,6-lutidine (5 equiv) were added to a solution of 2 (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.

The synthetic route of 1101120-05-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kendall, Jackie D.; Giddens, Anna C.; Tsang, Kit Yee; Frederick, Raphael; Marshall, Elaine S.; Singh, Ripudaman; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 58 – 68;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 76041-73-1, 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.76041-73-1, name is 3-Bromo-5-(trifluoromethyl)pyridin-2-ol, molecular formula is C6H3BrF3NO, molecular weight is 241.9933, as common compound, the synthetic route is as follows.

A mixture of 3-bromo-5-(trifluoromethyl)pyridin-2-ol (37.75g, 0.16 mol) and phosphorus(lll) oxychloride (POCI3; 75 mL) is stirred at 1000C for 5 hours. After cooling to room temperature, the mixture is poured into ice-water, and extracted with CH2CI2 twice. The combined organic layer is washed with NaHCO3 aq., brine, dried over MgSO4, filtered and concentrated in vacuo. The crude mixture is purified by flash column chromatography to give 3-bromo-2-chloro-5-trifluoromethylpyridine as a white solid. 1H-NMR (400MHz, CDCI3), delta (ppm): 8.17 (m, 1H), 8.62 (d, 1 H).

Statistics shows that 76041-73-1 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-5-(trifluoromethyl)pyridin-2-ol.

Reference:
Patent; NOVARTIS AG; WO2008/58961; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 149806-06-4, 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.149806-06-4, name is 6-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.01, as common compound, the synthetic route is as follows.

6-bromo-pyridine-3-carbaldehyde (5 g, 26.9 mmol, 1.0 eq.) and 4-ethyl-piperidine was dissolved in dichloromethane (100 ml), stirred for 2 hours, acetic acid was added portionwise inside borohydride sodium (6.2 g, 29.2 mmol, 1.1 eq). After 16 hours of reaction, an aqueous solution of sodium hydroxide was added thereto 2 mol/L to adjust the PH to alkaline, extracted with dichloromethane, and concentrated under reduced pressure to give a white solid of 1-(6-bromopyridin-3-yl)methyl-4-ethylpiperidine (6.98g, yield: 91.4%).

The chemical industry reduces the impact on the environment during synthesis 149806-06-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangzhou Kaisheng Beite Pharmaceutical Co., Ltd.; Cai, Xiong; Qian, Changgeng; Liu, Bin; Li, Junqi; Lin, Mingsheng; Qing, Yuanhui; Weng, Yunwo; Wang, Yanyan; Xue, Weicai; You, Huajin; Zhou, Shiqing; (67 pag.)CN105622638; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 130722-95-1, 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 130722-95-1, name is 3-(Benzyloxy)-5-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

10d. 3-amino-5-benzyloxypyridine The product of Example 10c above (41.3 g 156 mmol), copper(I) bromide (22.43 g 156 mmol), MeOH (275 mL), and liquid NH3 (50 mL) were combined in a stainless steel reactor and heated to 130 C. for 24 hours. The mixture was allowed to cool to ambient temperature, then concentrated. The residue was suspended in 300 mL of saturated aqueous Na2 CO3 and extracted with CH2 Cl2. The combined CH2 Cl2 solutions were washed with brine, dried (MgSO4), and concentrated. The crude product was chromatographed (silica gel; hexane/EtOAc, 9:1 to 7:3) to afford the title compound (15.6 g, 50%): 1 H NMR (CDCl3, 300 MHz) delta: 8.21-8.29 (m, 2H), 7.44-1.26 (m, 6H), 5.10 (s, 2H); MS (CI/NH3) m/z 201 (M+H)+.

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 130722-95-1, 3-(Benzyloxy)-5-bromopyridine.

Reference:
Patent; Abbott Laboratories; US6133253; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6980-08-1, 4-Chloro-3-nitropyridin-2-amine, 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, Computed Properties of C5H4ClN3O2, blongs to pyridine-derivatives compound. Computed Properties of C5H4ClN3O2

Dry DMSO (20 mL) was added to NaH (1.029 g of a 60% dispersion in mineral oil, 25.7 mmol) in a round bottom flask under argon. After 5 minutes, solid fert-butyl 2-fluoro-4- hydroxyphenylcarbamate (5.59 g, 24.6 mmol) was added in three portions, giving a dark solution, which, after 15 minutes of stirring at room temperature, was treated with 4-chloro-3-nitropyridin-2-amine (4.23 g, 24.4 mmol) at once. The dark red solution was heated to 0C for 1 hour and allowed to cool down to room temperature. EtOAc (150 mL) and H20 (200 mL) were subsequently added to the solution and the organic layer was isolated. The aqueous layer was extracted with EtOAc (3 x 100 mL) and the combined organic layers were washed once with saturated NaHC03 (150 mL), dried (MgS04), filtered, and concentrated to dryness to give a bright yellow solid. This material was used in the next step without further purification.Yield: 8.68 g (98%). 1H-NMR (DMSO-d6), delta (ppm), J (Hz): 1.46 (s, 9H, C(CH3)3), 6.08 (d, 1 H, PyrH), 7.01 (m, 1 H, ArH), 7.18 (br s, 2H, NH2), 7.22 (m, 1 H, ArH), 7.67 (m, 1 H, ArH), 8.04 (d, 1 H, PyrH), 9.03 (s, 1 H, NHBoc); 19F-NMR (DMSO-d6), delta (ppm): -120.7; LC-MS (4.72 min): m/z calcd. for C,6H17FN405 [M+H+]: 365.0; found:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6980-08-1, 4-Chloro-3-nitropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL (THE); SPRINGER, Caroline; NICULESCU-DUVAZ, Ion; MARAIS, Richard; NICULESCU-DUVAZ, Dan; ZAMBON, Alfonso; MENARD, Delphine; WO2011/92469; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem