Tag: M.W:200-300

Synthetic Route of 118650-08-1, 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 118650-08-1, name is Methyl 2-(5-bromopyridin-3-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows.

A solution of palladium acetate (1.4 mg, 0.00623 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (5.3 mg, 0.0124 mmol) and potassium phosphate (27.6 mg, 0.1246 mmol) in water (0.020 mL) and toluene (0.100 mL) was stirred for three minutes. Then, a solution of (5-bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 15.2 mg, 0.0659 mmol) and (E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl) – phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol (Example 26-(5); 26.9 mg, 0.0471 mmol) in toluene (0.12 mL) was added, and the mixture was stirred in a nitrogen atmosphere at 100C for one hour. After filtration through cotton plug, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate = 3/2) to give the title compound (5.0 mg, 17%). 1H-NMR (chloroform-d): 0.65 (t, 6H, J=7.2Hz), 1.60 (brs, 1H), 2.12 (q, 4H, J=7.2Hz), 2.24 (s, 6H), 3.69 (s, 2H), 3.73 (s, 3H), 6.16 (d, 1H, J=15.6Hz), 6.97-7.05 (m, 5H), 7.36-7.43 (m, 2H), 7.66 (s, 1H), 8.43 (d, 1H, J=6.9Hz).

According to the analysis of related databases, 118650-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76041-73-1, 3-Bromo-5-(trifluoromethyl)pyridin-2-ol, 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, Quality Control of 3-Bromo-5-(trifluoromethyl)pyridin-2-ol, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-5-(trifluoromethyl)pyridin-2-ol

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 (31.90 g, 79 % yield) as a white solid. 1H-NMR (400MHz, CDCI3), delta (ppm): 8.17 (m, 1H), 8.62 (d, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76041-73-1, 3-Bromo-5-(trifluoromethyl)pyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/73934; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1052714-46-1, 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.1052714-46-1, name is 6-Bromo-5-fluoropicolinic acid, molecular formula is C6H3BrFNO2, molecular weight is 219.9959, as common compound, the synthetic route is as follows.

To a solution of 6-bromo-5-fluoropicolinic acid (1.0 equiv.) in methanol (0.2 M) was added H2SO4 (4.2 equiv.) and the reaction was stirred at room temperature for two hours. Upon completion of the reaction as monitored by LC/MS, the reaction was diluted with ethyl acetate and quenched slowly with saturated aqueous NaHCO3. The reaction was poured into a separatory funnel and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate, filtered, and concentrated in vacuo to provide methyl 6-bromo-5-fluoropicolinate as a white solid (>99%). LC/MS=233.9/235.9 (M+H), Rt=0.69 min.

The chemical industry reduces the impact on the environment during synthesis 1052714-46-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Burger, Matthew; Nishiguchi, Gisele; Machajewski, Timothy D.; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225062; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 685517-71-9, name is 2,6-Difluoro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H2F2IN

To a solution of 4-(5-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)thiazole (300 mg, 1.29 mmol) in DMSO (5 mL) was added 2,6-difluoro-4-iodopyridine (373 mg, 1.55 mmol) and NaHC03 (542 mg, 6.45 mmol) and the resulting mixture was stirred for 18 hrs at 80 C. After being cooled to rt, the resulting reaction mixture was filtered and the filtrate was diluted with brine and extracted in DCM (30 mL) for three times. The combined organic layer was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by column chromatography (eluting with DCM/MeOH=20/l, v:v) to give 4-[6-(6-fluoro-4-iodo-2-pyridyl)- 5-methyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]thiazole (520 mg) as yellow solid.

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, 685517-71-9, 2,6-Difluoro-4-iodopyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; WANG, Yongguang; YANG, Song; (84 pag.)WO2018/83081; (2018); 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.14529-54-5, name is 3,5-Dibromo-1-methylpyridin-2(1H)-one, molecular formula is C6H5Br2NO, molecular weight is 266.92, as common compound, the synthetic route is as follows.Application In Synthesis of 3,5-Dibromo-1-methylpyridin-2(1H)-one

Step 5: A mixture of 105d (2.06 g, 10 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (2.65 g, 10 mmol), Pd2(dba)3 (91.6 mg, 0.1 mmol) Xant-phos (116 mg, 0.2 mmol), Cs2CO3(9.78 g, 30 mmol) in dioxane (100 mL) was degassed and stirred at 100 C. for 16 h under nitrogen. The reaction mixture was concentrated and the residue was purified by silica gel chromatography (EA/PE=5/1) to give N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-ylamino)ethyl)acrylamide 105e (2.54 g, 65%) as yellow solid. MS-ESI: [M+H]+ 394.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14529-54-5, 3,5-Dibromo-1-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Crawford, James John; Wei, BinQing; Young, Wendy B.; US2015/158846; (2015); 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.1196073-28-5, name is Methyl 4,6-dichloro-2-methylnicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.05, as common compound, the synthetic route is as follows.Quality Control of Methyl 4,6-dichloro-2-methylnicotinate

To a stirred suspension of sodium hydride (60% in mineral oil, 85 mg, 2.14 mmol) in DMF (4 mL) was added, dropwise, ethyleneglycol mono t-butyl ether (278 mg, 2.35 mmol). the reaction mixture was stirred for 25 min. A solution of 4,6-dichloro-2-methyl- nicotinic acid methylester (0.5g, 2.14 mmol) in DMF (1.5 mL) was added to the reaction mixture was stirred at RT overnight. The reaction mixture was quenched with water, extracted with EtOAc, the organic layer washed with water, brine, dried over Na2SO4 and volatiles removed. The residue was purified by column chromatography using 0-50% EtOAc/Hexanes to provide compound Villa (260 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1196073-28-5, Methyl 4,6-dichloro-2-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2009/140553; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 121912-29-6, 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. 121912-29-6, name is Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Step 2: Synthesis of 1-(4-pyridyl)-4-piperidinecarboxylic acid hydrochloride: 2.95 g (12.6 mmol) of ethyl 1-(4-pyridyl)-piperidine-4-carboxylate was stirred in 100 ml of dioxane. After adding 50 ml of 1 N hydrochloric acid, the obtained mixture was stirred at 95C for 20 hours. The solventwas evaporated under reduced pressure to obtain the title compound. Yield: 3.21 g (11.5 mmol) (91 %) MS (ESI, m/z) 207 (MH+) H-NMR (DMSO-d6) delta 1.54 (2H, t), 1.90 (2H, d), 2.60-2.70 (1H, m), 3.30 (2H, t), 4.10 (2H, d), 7.19 (2H, d), 8.20 (2H, d)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,121912-29-6, Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Ajinomoto Co., Inc.; EP1065200; (2001); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-36-4, 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. 884494-36-4, name is 3-Bromo-2-chloro-5-fluoropyridine, molecular formula is C5H2BrClFN, 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 urea compound with hydrogen peroxide (1 : 1) (1.34, 14.3 mole) and trifluoroacetic anhydride (2 mL, 14.3 mole) in 10 mL dichloromethane at 0 C for at least 15 minutes was added 3- fluoro-5-bromopicolinonitrile (500 mg, 2.38 mmol). The reaction mixture was stirred at 40 C for 2 hours. The reaction quenched with saturated aqueous NaHC03 (20 mL) and then extracted with DCM (20 mL x 5). The combined organics were dried over anhydrous Na2SC”4 and concentrated to give the crude title compound, which was carried forward without purification. MS: 226, 228 (M+l).

According to the analysis of related databases, 884494-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John, J., III; BAO, Jianming; DENG, Qiaolin; EGBERTSON, Melissa; FERGUSON, Ronald, III; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; MENG, Zhaoyang; NA, Meng; RUDD, Michael, T.; SELYUTIN, Oleg, B.; TELLERS, David, M.; TONG, Ling; ZHANG, Fengqi; (195 pag.)WO2019/5587; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63897-12-1, 2,4-Dichloro-6-methyl-3-nitropyridine, 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, 63897-12-1, blongs to pyridine-derivatives compound. Safety of 2,4-Dichloro-6-methyl-3-nitropyridine

EXAMPLE 1022-[2-(1 ,3-benzothiazol-5-yl)-1 H-imidazol-4-yl]-6-methyl-1 -[2-(methyloxy)ethyl]-4-(4- mor holinyl)-1 H-imidazo[4,5-c]pyridineStep 1 . 2-chloro-6-methyl-N-[2-(methyloxy)ethyl]-3-nitro-4-pyridinamineTo a solution of 2,4-dichloro-6-methyl-3-nitropyridine (1 g, 4.83 mmol) and triethylamine (0.741 ml, 5.31 mmol) in Nu,Nu-Dimethylformamide (DMF) (1.959 ml) at 0 C was added a solution of 2-methoxyethlyamine (0.424 ml, 4.88 mmol) in Nu,Nu-Dimethylformamide (DMF) (0.535 ml). Removed from ice bath and stirred at rt overnight. LCMS showed mainly desired product along with a small amount of the undesired regioisomer as well as the bis addition product. Quenched with water and diluted with Et20. Separated and extracted twice more with Et20. Washed combined organics with water twice, then with brine, dried on MgS04, filtered and concentrated. Purified via Biotage FCC (0-20% EtOAc / hex) Desired and bis-addition product co-eluted. Combined all product-containing fractions and concentrated resulting in a bright yellow solid. Suspended in hexanes, sonicating to break up large particles. Sonicated for 20 min. Filtered and collected bright yellow solid that was pure desired product: 2-chloro-6-methyl-N-[2-(methyloxy)ethyl]-3-nitro-4- pyridinamine (466 mg, 1.897 mmol, 39.3 % yield). MS (m/z): 246.1 (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,63897-12-1, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; BODMER, Vera, Q.; CASILLAS, Linda, N.; DEMARTINO, Michael, P.; KING, Bryan, W.; LAKDAWALA SHAH, Ami; LEISTER, Lara, Kathryn; WANG, Gren, Z.; WISNOSKI, David, Duff; HARRIS, Philip, A.; RAMANJULU, Joshi, M.; ROMANO, Joseph, J.; WILSON, Matthew, A.; WO2011/123609; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 824429-51-8, Adding some certain compound to certain chemical reactions, such as: 824429-51-8, name is tert-Butyl (2-(hydroxymethyl)pyridin-3-yl)carbamate,molecular formula is C11H16N2O3, 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 824429-51-8.

N- [2- (hydroxymethyl) pyridin-3-yl] carbamic acid tert-butyl ester(0.15 g) in dichloromethane (1 mL)Thionyl chloride (0.096 g) was added, and the mixture was stirred at room temperature for 1 hour.The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and the crude product was extracted with dichloromethane. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane)To give N- [2- (chloromethyl) pyridin-3-yl] carbamic acid tert-butyl ester (0.12 g).A mixture of the product (0.12 g), dichloromethane (2 mL), potassium cyanide (0.039 g), tetrabutylammonium hydrogen sulfate (0.017 g) and water (0.5 mL) was stirred at room temperature for 3 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the crude product was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane)To give N- [2- (cyanomethyl) pyridin-3-yl] carbamic acid tert-butyl ester.Concentrated hydrochloric acid (0.072 g) and 10% palladium on carbon (50% wet, 0.03 g) were added to the product methanol (3 mL) – dichloromethane (3 mL) mixture, and the mixture was stirred at room temperature under a hydrogen atmosphere (0.32 MPa) Followed by stirring. The reaction mixture was passed through a celite pad and the filtrate was concentrated under reduced pressure. The residue was purified by aminopropyl silica gel column chromatography (eluent: ethyl acetate / methanol) to give the title compound (0.011 g). Structural formula, spectral data and purification conditions are shown in Table 26.

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. 824429-51-8, tert-Butyl (2-(hydroxymethyl)pyridin-3-yl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Hirasawa, Hideaki; Tanada, Fumiya; Mutai, Yousuke; Fushimi, Nobuhiko; Kobayashi, Junichi; Kijima, Yoshiro; (267 pag.)JP2018/108988; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem