Tag: M.W:200-300

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. 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde, molecular formula is C7H6BrNO2, 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. Safety of 5-Bromo-2-methoxyisonicotinaldehyde

To a solution of the commercially available 5-bromo-2- methoxyisonicotinaldehyde (5.0 g, 23.2 mmol, leq) in MeOH was added triethylamine (12eq), Pd (dppfjC^ (O. leq) at 70C under 50 psi of CO gas in a steel bomb for 16h. Subsequent reaction work-up and flash column chromatography on silca-gel afforded 1.8 g (39% yield) of the desired compound, methyl 4-formyl-6- methoxynicotinate; LCMS [M + H]+ 196.

With the rapid development of chemical substances, we look forward to future research findings about 936011-17-5.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 29241-65-4, name is 5-Bromo-2-chloronicotinic acid, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To 0.5 L flask charged with 5-Bromo-2-chloronicotinic acid (25.0 g, 106.4 mmol) in MeOH (250 mL) was added H2SO4 (5 mL). The mixture was heated to 60 C., stirred for 1.5 day. LC-MS indicated full conversion of starting material at this time. The reaction was cooled to RT and the volatile components removed in vacuo. The crude residue was dissolved in EtOAc (300 mL), quenched with sat. aqueous Na(HCO3)2 (200 mL). The organic layer was separated, washed with brine, dried over MgSO4 and concentrated to afford the compound, methyl-5-bromo-2-chloronicotinate, as a while solid (quantitative yield). LC-MS (M+H)=250.1.

The synthetic route of 29241-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Conn, P. Jeffrey; Lindsley, Craig W.; Stauffer, Shaun R.; Manka, Jason; Jacobs, Jon; Zhou, Ya; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Jones, Carrie K.; US2012/172391; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-06-6, Methyl 5-bromo-4-methylpicolinate, 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, Product Details of 886365-06-6, blongs to pyridine-derivatives compound. Product Details of 886365-06-6

Into a vial was weighed methyl 5-bromo-4-methylpicolinate (300 mg, 1.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), bis(pinacolato)diboron (364 mg, 1.43 mmol), and potassium acetate (384 mg, 3.91 mmol). Under nitrogen, anhydrous 1,4-dioxane (6.5 mL) was added and the vial was sealed. The reaction mixture was stirred at 120 C. for 18 h. After cooling to rt, under nitrogen, to the reaction vessel was added (+-)-(trans)-N-(8-amino-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (447 mg, 1.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), and potassium carbonate (540 mg, 3.91 mmol), and water (1.3 mL). The vial was sealed and stirred at 100 C. for 23 h. The reaction mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-85:15) to afford the target compound as a brown solid (126 mg, 21% over 2 steps); 1H NMR (400 MHz, DMSO-d6) delta 10.95 (s, 1H), 9.38 (s, 1H), 8.71 (s, 1H), 8.28 (s, 1H), 8.01 (s, 1H), 7.56 (s, 1H), 7.37 (br s, 2H), 7.29 (s, 1H), 7.05 (s, 1H), 3.91 (s, 3H), 3.77 (s, 3H), 2.25-2.16 (m, 2H), 1.90 (s, 3H), 1.43-1.34 (m, 1H), 1.24-1.14 (m, 1H).

The synthetic route of 886365-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 103058-87-3, 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 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 1; 4- (5-formgammal-6-methoxypyridin-3-gammal) benzonitrile; A mixture of 5-bromo-2-methoxynicotinaldehyde (2.0 g) synthesized by a known method (Journal of Heterocyclic Chemistry 1985, 22(6), 1583-1592), (4- cyanophenyl) boronic acid (1.36 g) , Pd(PPh3)4 (0.32 g) and potassium carbonate (2.6 g) in THF (20 mL) and water (10 mL) was heated under reflux for 12 hrs. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated under reduced pressure. The obtained residue was crystallized from acetone/ethanol/IPE to give the title compound (0.93 g) as white crystals . melting point: 157C

According to the analysis of related databases, 103058-87-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/89031; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 10177-08-9, 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 10177-08-9, name is 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-Oxo-5-phenyl-l,2-dihydro-pyridine-3-carboxylic acid (44 g, 0.20 mmol) in tetrahydrofuran (5 mL) were successively added aniline (20 muL, 0.23 mmol), hydroxybenzotriazole (30 mg, 0.23 mmol), dimethylaminopyridine (27 mg, 0.23 mmol) and EDC (43 mg, 0.23 mmol). The reaction mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with DCM containing 10percent of MeOH to afford the title compound as a white solid (20 mg, 34percent yield). MS (ES+) 291. deltaH (DMSOd6) 7.2 (3H, m), 7.9 (IH, t), 8.5 (IH, d), 8.6 (2H, m), 9.3 (IH, s).

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 10177-08-9, 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/65946; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22282-96-8, 2-Bromo-6-methyl-5-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, 22282-96-8, blongs to pyridine-derivatives compound. Product Details of 22282-96-8

To a stirred solution of 6-bromo-2-methyl-3-nitropyridine (15 g, 69.12 mmol) in ethanol (280 mL) was added iron powder (57.9 g, 1036 mmol) followed by conc HCl (30 mL). The reaction mixture was stirred for 6 h at 100 C., after completion of reaction (monitored by TLC), reaction mixture was cooled to room temperature, filtered through celite. Filterate was basified with saturated NaHCO3 solution, extracted with EtOAc. Organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product was used in next step without further purification to afford desired compound (5.6 g, 65%) as an off-white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-96-8, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; BOCK, Mark; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (141 pag.)US2016/347717; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine, molecular formula is C8H7BrN2, 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. Product Details of 116355-18-1

The compound of example 146 (8 g, 37.9 mmol) was treated with 6-methylpyridin-3- ylboronic acid (5.71 g, 41 .7 mmol) in the presence of [1 ,1 ‘-Bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.495 g, 0.606 mmol) and sodium carbonate (6.03 g, 56.9 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 8.0 g (95 %); 1 H NMR (DMSO-d6, 300 MHz): delta 2.2 (s, 3H, CH3), 2.54 (s, 3H, CH3), 7.35-7.37 (d, 1 H, J=8.1 Hz, Ar), 7.50-7.53 (d, 1 H, J=8.7 Hz Ar), 7.53 (s, 1 H, Ar), 7.76-7.80 (dd, 1 H, J=2.4 Hz & J=5.7 Hz, Ar Ar), 7.8 (s, 1 H, Ar), 8.4 (s, 1 H, Ar), 8.49-8.50 (d, 1 H, J=1 .8 Hz, Ar); MS (ES+): m/e 224.1 (M+1 ).

With the rapid development of chemical substances, we look forward to future research findings about 116355-18-1.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); 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 856013-04-2, name is 6-Bromopyridine-2-sulfonamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

c) 6-(8-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-pyridine-2-sulfonamide6-Bromo-pyridine-2-sulfonamide (65mg, 0.27 mmol), 7-(4,4,5,5-Tetramethyl- [l,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-naphthalen-l-one (97mg, 0.36 mmol), tetrabutylammonium bromide (TBAB) (lOmg, 0.04 mmol) and Pd(PPh3)2Cl2 (13mg, 0.02 mmol) in dioxane:water (1.2 mL/0.6 mL) were heated at 1000C in a microwave reactor for 1 hour. After this time, water was added and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with water and brine and dried over Na2SO4. Concentration afforded a brown solid which was triturated with Et2O. An off-white solid was obtained. Analysis (NMR) showed presence of impurities but the compound was on-reacted without further purification. NMR 1H (d6-DMSO, ppm): 8.6 (d, J = 2.1 Hz, IH), 8.36 (dd, J = 8.1 and 2.1 Hz, IH), 8.20 (dd, J = 9.03 and 1 Hz, IH), 8.11 (t, J = 7.6 Hz, IH), 7.85 (dd, J = 7.6 and 1 Hz, IH), 7.53-7.50 (m, 3H), 3.01-2.98 (m, 2H), 2.66-2.62 (m, 2H), 2.10-2.04 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 856013-04-2.

Reference:
Patent; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; WO2009/39553; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 117846-58-9, 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. 117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine, molecular formula is C7H7Br2N, 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 stirred solution of 2 (3.15 g, 11.87 mmol) in anhydrous THF (50 mL) was added dropwise a 2.5 M solution of n-BuLi in hexane (5.12 mL, 12.80 mmol) at 195 K. The reaction was stirred for 30 min at thistemperature, a solution of (2,5-Dimethyl-3-thienyl)perfluorocyclopentene (3.97 g,13.06 mmol) in THF (5 mL) was added. The reaction solution was stirred for 1 hat this temperature. The reaction was allowed to warm to room temperature, andquenched with water (15 mL). The product was extracted with diethyl ether. Theorganic layers were combined, dried over anhydrous Na2SO4,filtered, and concentrated in vacuo. Column chromatography on Al2O3(hexane) afforded diarylethene 4 (1.62 g, 29%) as a colorless crystal, mp 96-97 C; 1H NMR(400 MHz, CDCl3): delta 7.29(s, 1H, pyridine-H), 6.64 (s, 1H, thiophene-H), 2.38 (s, 3H, -CH3), 2.37(s, 3H, -CH3), 1.93 (s, 3H, -CH3), 1.84 (s, 3H, -CH3);13C NMR (100 MHz,CDCl3) delta 145.20, 141.66, 141.00,140.54, 137.87, 135.98, 132.68, 124.51, 123.61, 21.72, 17.43, 15.04, 14.26; IR(KBr, nu, cm-1): 3128, 1637,1587, 1400, 1274, 1126, 1188, 1060, 1004, 894, 826, 734, 707; LRMS, ESI+m/z 470.1 (MH+, C18H14BrF6NS requires 469.0); Anal. Calcd for C18H14BrF6NS: Calcd C, 45.97; H, 3.00; N, 2.98. Found C, 45.91; H, 3.02; N, 2.96

According to the analysis of related databases, 117846-58-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zheng, Chunhong; Liu, Gang; Pu, Shouzhi; Tetrahedron Letters; vol. 54; 43; (2013); p. 5791 – 5794;,
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.603311-76-8, name is Ethyl 2-(6-bromoimidazo[1,2-a]pyridin-3-yl)acetate, molecular formula is C11H11BrN2O2, molecular weight is 283.12, as common compound, the synthetic route is as follows.Recommanded Product: Ethyl 2-(6-bromoimidazo[1,2-a]pyridin-3-yl)acetate

General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetates 3 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.) and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture was added DBU (456 mg, 3 mmol, 3.0 equiv.). The mixture was stirred for 12 hours at room temperature till the reaction was complete. To the resulting mixture was added saturated ammonium chloride solution (25 mL), and the mixture was then extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 4 was purified using column chromatography on silica gel using an appropriate eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,603311-76-8, Ethyl 2-(6-bromoimidazo[1,2-a]pyridin-3-yl)acetate, and friends who are interested can also refer to it.

Reference:
Article; Zhou, Mingwei; Hu, Yimin; En, Ke; Tan, Xuefei; Shen, Hong C.; Qian, Xuhong; Tetrahedron Letters; vol. 59; 14; (2018); p. 1443 – 1445;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem