Month: April 2022

Reference of 121643-44-5, 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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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.

Preparation Example 36 2-Methoxy-3-(trifluoromethyl)pyridine (8 g), 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (17 g), and trifluoroacetic acid (32 mL) were mixed, followed by stirring at room temperature for 22 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added diisopropyl ether. The precipitated solid was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine (9.4 g) as an oil.

According to the analysis of related databases, 121643-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; KOIKE, Takanori; NEGORO, Kenji; TANAKA, Hiroaki; MAEDA, Jun; YOKOYAMA, Kazuhiro; TAKAMATSU, Hajime; (146 pag.)EP3153511; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 133928-73-1, Adding some certain compound to certain chemical reactions, such as: 133928-73-1, name is 2-Chloro-3-methyl-4-pyridinecarboxylic Acid,molecular formula is C7H6ClNO2, 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 133928-73-1.

[01652] Step 4: Synthesis of methyl 2-chl hylpyridine-4-carboxylate[01653] To a stirred solution of 2-chloro-3-methylpyridine-4-carboxylic acid (780 mg, 4.5 mmol) in anhydrous DMF (5.0 ml), was added potassium carbonate (1 .25 g, 9.1 mmol), followed by methyl iodide (0.42 ml, 6.8 mmol) dropwise. A further 4 ml of DMF was added and the reaction mixture was stirred at room temperature under nitrogen for 18.5 hours. The solvent was removed in-vacuo and the residue was then partitioned between CI b b (20 ml) and water (20 ml). The layers were separated and the aqueous layer was extracted with CH2C12 (3 x 15 ml). The combined organic layers were washed with water (2 x 30 ml), brine (40 ml), dried (MgS0 ), filtered and concentrated in-vacuo. The residue was purified by column chromatography (l Og SNAP cartridge, Isolera, 0-6% ethyl acetate:heptanes) to give the title compound (591 mg, 59%) as a colourless oil. LC-MS 84%, m/z = 185.9, 1 87.9; NMR (500 MHz, Chloroform-d) delta ppm 8.33 (d, J=5.04 Hz, 1 H) 7.54 (d, J=5.04 Hz, 1 H) 3.95 (s, 3 H) 2.60 (s, 3 H).

According to the analysis of related databases, 133928-73-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 717843-51-1, Adding some certain compound to certain chemical reactions, such as: 717843-51-1, name is 3-Bromo-2-methoxy-4-methylpyridine,molecular formula is C7H8BrNO, 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 717843-51-1.

To a pressure tube was added 3-bromo-2-methoxy-4-methylpyridine (396 mg, 1.96 mmol), bis(pinacolato)diboron (597 mg, 2.35 mmol), Pd(dppf)2Cl2 (143 mg, 0.20 mmol), potassium acetate (384 mg, 3.92 mmol) and 1,4-dioxane (15 mL). The mixture was stirred at 95 C. for 4 hours. The residue was purified by silica gel flash chromatography (petroleum ether/ethyl acetate, 4:1) to give 2-methoxy-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (250 mg, 51% yield) as a colourless oil. LCMS (ESI): [M+H]+=249.3.

According to the analysis of related databases, 717843-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate, 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, Formula: C10H11BrClNO2, blongs to pyridine-derivatives compound. Formula: C10H11BrClNO2

Example 14A methyl 2-(5-bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-8-carboxylate Methyl 4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-8-carboxylate (500 mg), EXAMPLE 1D (572 mg), and triethylamine (0.545 mL) in anhydrous dimethylsulfoxide (6.5 mL) was heated to 100 C. overnight, and the mixture was then cooled to room temperature. The reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (15 mL) and ethyl acetate (15 mL). The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2*15 mL). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel with 0-40% ethyl acetate/hexanes to provide the title product.

The synthetic route of 1235036-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; WANG, LE; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96120; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 90395-45-2, 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 90395-45-2, name is 1-(4-(Pyridin-3-yl)phenyl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

1-(4-Pyridin-3-ylphenyl)-ethanone (50 g, 253.51 mmole),4-bromo-benzaldehyde (44.67g, 241.44mmole),Add 893 ml of ethanol and stir in the reaction flask.Finally, sodium tert-butoxide (34.77 g, 362.16 mmole) was added and stirred at room temperature.After the reaction has been completed, add 200 ml of deionized water and stir to filter.After filtering the solid with deionized water and methanol, the solid was filtered with 100 ml of deionized water and 200 ml of methanol for 30 minutes.The solid was dried twice to obtain 48 g of pale yellow solid 3-(4-bromophenyl)-1-(4-pyridin-3-ylphenyl)-propanone (3-(4-Bromo-phenyl)-1 -(4-pyridin-3-yl-phenyl)-propanone),The yield was 54.58%.

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 90395-45-2, 1-(4-(Pyridin-3-yl)phenyl)ethanone.

Reference:
Patent; Yulei Optoelectric Technology Co., Ltd.; Huang Helong; Guo Huangming; Zhao Dengzhi; Lin Qizhen; Zhang Minzhong; (29 pag.)CN109988159; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, 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, COA of Formula: C5H2BrClIN, blongs to pyridine-derivatives compound. COA of Formula: C5H2BrClIN

1-(5-Bromo-2-chloropyridin-3-yl)-2-(2-chloro-3-fluoro-6-methoxyphenyl)propan-1 -olA solution of 5-bromo-2-chloro-3-iodopyridine (0.750 g, 2.36 mmol) in anhydrous THF (5.5 mL) was cooled to -50 C and dropwise charged with 2.0 M of isopropylmagnesium chloride in THF (1.41 mL, 2.83 mmol) over an 8 min period and the mixture was stirred at -50 C for an additional 30 min. After 30 min., the mixture was charged with 2-(2-chloro-3-fluoro- 6-methoxyphenyl)propanal (0.766 g, 3.53 mmol) and stirred at -40 C for 1 h then allowed to warm to 0 C and charged with brine (10 mL) and allowed to stir for 15 min. The reaction mixture was partitioned between EtOAc and H20 and separated. The aqueous was re- extracted with EtOAc (3x) and the combined organic fractions were dried over Na2S04, filtered and concentrated in vacuo resulting in 930 mg of a crude oil/solid mixture. The mixture was recrystallized from 20% EtOAc in hexanes resulting in 245 mg of a white solid (diastereomer A). The mother liquor was purified by chromatography on silica gel [Jones Flashmaster, 20 g cartridge, eluting with 12% EtOAc in hexanes] resulting in 31 1 mg of a white foam (mainly diastereomer B). These two diastereomers were combined for the subsequent oxidation step. Diastereomer A: 1H NMR (400 MHz, CDCI3): delta = 1.34 (d, J = 6.23 Hz, 3H), 3.62 (br. s., 1 H), 3.89 (br. s., 3H), 5.43 (br. s., 1 H), 6.70-6.80 (m, 1 H), 6.94-7.03 (m, 1 H), 8.1 1 (d, J = 1.5 Hz, 1 H), 8.30 (d, J = 1.5 Hz, 1 H). MS (ES+): m/z 407.73, 409.77, 41 1 .74 [MH+]. HPLC: tR = 3.12 min (nonpolar_5min, ZQ3). Diastereomer B: 1H NMR (400 MHz, CDCI3): delta = 1 .41 (d, J = 7.3 Hz, 3H), 3.93-3.97 (m, 3H), 3.97-4.05 (m, 1 H), 5.44 (br. s., 1 H), 5.55 (dd, J = 4.6, 6.6 Hz, 1 H), 6.83 (dd, J = 4.3, 9.1 Hz, 1 H), 7.03 (dd, J = 8.1 , 9.1 Hz, 1 H), 7.76 (d, J = 0.5 Hz, 1 H), 8.33 (d, J = 2.5 Hz, 1 H). MS (ES+): m/z 407.73, 409.76, 41 1.74 (100/68/17) [MH+]. HPLC: fR = 3.35 min (nonpolar_5min, ZQ3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; LI, An-Hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WO2011/143646; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 960289-03-6 , The common heterocyclic compound, 960289-03-6, name is 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, molecular formula is C7H6BrNOS, 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.

Preparation 29; 2-(4-Chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one; Combine 2-bromo-6H-thieno[2,3-c]pyridin-7-one (25.0 g, 108.7 mmol), A- chlorophenylboronic acid (18.7 g, 119.5 mmol), sodium carbonate (23.5 g, 217.3 mmol), ethanol (121 mL), 1 ,2-dimethoxyethane (604 mL), and water (121 mL). Purge the mixture with nitrogen for 20 min. Add tetrakis(triphenylphosphine)palladium (3.77 g, 3.26 mmol). Heat the reaction mixture at 85 0C overnight. Allow the reaction to cool to RT. Reduce the reaction solvent volume to half on a rotory evaporator. Filter the mixture with water (2 x 400 mL), ether (400 mL), and ethylacetate (20 mL) and dry the solids in vacuo at 40 0C to give 25.4 g (89%) of the title compound. LC-MS/ES m/z (35Cl) 262.0 [M+H]+.

The synthetic route of 960289-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146758; (2007); A2;,
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.71777-70-3, name is Ethyl 4-ethoxypicolinate, molecular formula is C10H13NO3, molecular weight is 195.22, as common compound, the synthetic route is as follows.HPLC of Formula: C10H13NO3

To a solution of ethyl 4-ethoxypicolinate (3.44 g, 17.43 mmol) and 4-methoxy acetophenone (2.62 g, 17.43 mmol) in THF (100 mL) and DMSO (50 mL) was added NaH (1.4 g, 34.80 mmol). The resulting mixture was stirred at 95 C. for 6 h. The reaction mixture was cooled to rt and quenched with water (100 mL). The mixture was extract with EtOAc (3×150 mL) and concentration to a yellow solid. The solid was washed with hexanes to afford the diketone (3.6 g, 69%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,71777-70-3, Ethyl 4-ethoxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281396; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, 89415-54-3, blongs to pyridine-derivatives compound. Formula: C6H8BrN3

6-Bromo-3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridineTo a solution of 5-bromo-N2-methylpyridine-2,3-diamine (720 mg, 3.56 mmol) inH2S04(1.90 muIota_, 35.6 mmol) at RT, NaN02(246 mg, 3.56 mmol) was added. The reaction mixture was stirred for 1 h after which time water was added to quench the reaction. EtOAc was added, and the layers were separated. The aqueous layer was extracted once with EtOAc, and the combined organic layers were washed once with brine. The organic layer was concentrated to give 694 mg (91 %) of the title compound. LC-MS m/z 212.8, 214.8 (M+H)+, 0.66 (ret. time).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89415-54-3, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (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.1190320-33-2, name is 6-Fluoro-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5FN2, molecular weight is 136.13, as common compound, the synthetic route is as follows.name: 6-Fluoro-1H-pyrrolo[3,2-b]pyridine

Step 3: l-(6-Fluoro-lH-pyrrolo[3,2-b]pyridin-3-yl)-N,N-dimethylmethanamine (25) 25 [00632] Paraformaldehyde (0.24 g, 8.1 mmol) and dimethylamine hydrochloride (0.66 g, 8.1 mmol) were added to a stirred solution of compound 24 (1.0 g, 7.35 mmol) in n-butanol (10 mL). The reaction was refluxed for 3 h. The solution was allowed to cool to rt and poured into 15% HCl (100 mL). The butanol layer was discarded and the water phase was adjusted to pH13- 14 with 2M NaOH. The resulting mixture was extracted with ethyl acetate (100 mLx3). The organic extracts were combined, washed with brine (100 mL), dried over anhydrous sodium sulfate, and concentrated to give compound 25 (1.0 g, 71% yield), which was used in the next reaction without purification. LC-MS: 194.02 (M+H), Ci0Hi2FN3. 1H NMR (CDC13, 400 MHz) S: 10.13 (br, 1H), 8.36 (s, 1H), 7.31-7.22 (m, 2H), 3.75 (s, 2H), 2.32 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1190320-33-2, 6-Fluoro-1H-pyrrolo[3,2-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; AKARNA THERAPEUTICS, LTD.; MOHAN, Raju; PRATT, Benjamin, Anthony; (297 pag.)WO2016/103037; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem