Month: April 2022

Application of 885277-48-5, 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.885277-48-5, name is Methyl 2-bromo-6-methylnicotinate, molecular formula is C8H8BrNO2, molecular weight is 230.06, as common compound, the synthetic route is as follows.

Na2C03 (8.43 g, 80 mmol) was added to a solution of methyl 2-bromo-6-methylnicotinate (6.1 g, 26.5 mmol) and methyl acrylate (6.08 mL, 67.1 mmol) in mixture of DMA (16.99 mL, 181 mmol) and toluene (55 mL) at room temperature. Then the reaction mixture was degassed for 15 min. Tri-r olyl phosphine (0.807 g, 2.65 mmol) and allylpalladium chloride dimer (0.4850 g, 1.326 mmol) were added and the reaction mixture was stirred at 115 C in sealed tube for 5 h. Filtered through pad of Celite, and the filtrate was concentrated under reduced pressure. The resultant crude compound was purified by flash column chromatography on 100-200 mesh silica gel using 20% EtO Ac/pet-ether as an eluent to obtained (///-methyl 2-(3-methoxy-3-oxoprop-l- en-l-yl)-6-methylnicotinate (3.30 g, 43.0% yield) as a colorless oil. 1H NMR (400 MHz, CDCE): d 8.53 (dd, /= 1.2, 15.2 Hz, 1H), 8.22 (d, /= 6.8 Hz, 1H), 7.20-7.11 (m, 2H), 3.94 (s, 3H), 3.82 (s, 3H), 2.60 (s, 3H). LCMS (ES) m/z 236.09 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 885277-48-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Anish; CHEUNG, Mui; EIDAM, Hilary Schenck; JOSHI, Hemant; SU, Dai-Shi; (128 pag.)WO2019/149959; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 194673-12-6, 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. 194673-12-6, name is Ethyl 6-oxo-2-(trifluoromethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate, molecular formula is C9H10F3NO3, 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 6-hydroxy-2-trifluoromethyl-4, 5-dihydro-pyridine-3-carboxylic acid ethyl ester (Description 14) (4. 7 g, 19. 8 mmol, 1 eq) and N-bromo succinimide (3.51 g, 19. 8 mmol, 1 eq) in 15 mL of carbon tetrachloride was heated under reflux for 20 h. The resulting precipitate was filtered off and the filtrate was concentrated under reduced pressure to afford a brownish solid that was purified by flash chromatography (silica gel, eluent gradient: from hexane/ethyl acetate 9: 1 to hexane/ethyl acetate 8: 2). The title compound was obtained as a white solid (4.3 g, yield = 92%). LC-MS (ESI+), MH+: 236.

According to the analysis of related databases, 194673-12-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; DOUGHTY, Jennifer, Margaret; WO2005/74939; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1033203-41-6 ,Some common heterocyclic compound, 1033203-41-6, molecular formula is C5H6BrN3, 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 mixture of 6-bromopyridine-3,4-diamine (100 mg, 0.53 mmol) and lH-pyrazole-4-carboxylic acid (60 mg, 0.53 mmol) in polyphosphoric acid (1 g) was heated in a sealed vial at 200 C for 18 h. The reaction mixture was diluted with water and made basic by addition of NaOH (50% aq.) and a white precipitate formed. The solid thus formed was collected by filtration and washed with water to afford the title compound (150mg, quant.). LCMS (ESI): [M+H]+ 264.1.

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. 1033203-41-6, 6-Bromopyridine-3,4-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 670253-37-9, 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.670253-37-9, name is 4-Chloro-5-iodopyridin-2-amine, molecular formula is C5H4ClIN2, molecular weight is 254.46, as common compound, the synthetic route is as follows.

General procedure: A mixture of 30 (500mg, 2.67mmol), Zn(CN)2 (188mg, 1.60mmol), Pd2(dba)3 (122mg, 0.13mmol), and dppf (148mg, 0.27mmol) was added degassed DMF/ H2O (99:1, 3.1mL). The reaction mixture was heated using conventional heating at 120C for 24h. The resulting mixture was cooled to rt, and sat. aq. NH4Cl/ conc. NH3/H2O (4:1:4, 10mL) was added resulting in precipitation. The mixture was cooled to 0C and filtered. The precipitate was washed with sat. aq. NH4Cl/conc. NH3/H2O (4:1:4, 10mL) and H2O at 5C and dried under vacuum affording the product as dark orange solid (279mg, 78%).

The chemical industry reduces the impact on the environment during synthesis 670253-37-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Petersen, Jette G.; S°rensen, Troels; Damgaard, Maria; Nielsen, Birgitte; Jensen, Anders A.; Balle, Thomas; Bergmann, Rikke; Fr°lund, Bente; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 404 – 416;,
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. 130284-52-5, name is 6-Bromo-5-chloropyridin-3-amine, molecular formula is C5H4BrClN2, 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. name: 6-Bromo-5-chloropyridin-3-amine

Pd2(dba)3 (176.56 mg, 0.19 mmol) and Xphos (183.83 mg, 0.39 mmol) were added to a solution of 6-bromo-5-chloropyridin-3-amine (800 mg, 3.86 mmol), 1 -methyl-3-(4,4,5,5-tetramethyl-i ,3,2-dioxaborolan-2-yl)-1H-pyrazole (1203.52 mg, 5.78 mmol) and K3P04 (2.456 g,11.57 mmol) in dioxane/H20 (6/1, 20 mE) under an N2 atmosphere. The mixture was stirred at 1000 C. overnight. The reaction solution was filtered and the filtrate was concentrated to give a crude product. The crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate from 100/0 to 0/100). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford 1 57a (530 mg, 5 9.0% yield) as a yellow solid. ECMS (ESI) mlz M+i: 209.1.

With the rapid development of chemical substances, we look forward to future research findings about 130284-52-5.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1452-94-4, Adding some certain compound to certain chemical reactions, such as: 1452-94-4, name is Ethyl 2-chloronicotinate,molecular formula is C8H8ClNO2, 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 1452-94-4.

A toluene solution (300 mL) of ethyl 2-chloronictinate (5.57 g), phenylboronic acid (4.76 g), tripotassium phosphate (8.91 g), 1,1′-bis (diphenylphosphino) ferrocene-palladiumdichloride dichloromethane complex (439 mg) was stirred under reflux for 4 hours in a nitrogen atmosphere. Water (100 mL) was added to the reaction solution, and the reaction solution was separated. The obtained organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified with silica gel column chromatography (hexane/ethyl acetate=96/4 to 75/25) to give ethyl 2-phenylnicotinate (5.27 g) as an oil. MS m/z 229 [M+H]

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. 1452-94-4, Ethyl 2-chloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; SUMITOMO DAINIPPON PHARMA CO., LTD.; FUSANO, Akira; KOBAYASHI, Tomonori; SAITO, Yasuhiro; KANAI, Toshio; (55 pag.)US2016/221948; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 72141-44-7 , The common heterocyclic compound, 72141-44-7, name is 4-Chloro-2-methoxypyridine, molecular formula is C6H6ClNO, 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.

(e); 10.0 g (69.9 mmol) of crude 4-chloro-2-methoxypyridine obtained in Step (d) was dissolved in 100 ml of dimethylformamide, and 37.2 g (279 mmol) of N-chlorosuccinimide was added, followed by stirring at room temperature for 12 hours. 400 ml of water was added to terminate the reaction, followed by extraction with ethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 9.10 g (crude yield: 73%) of crude 4,5-dichloro-2-methoxypyridine. 1H-NMR(CDCl3, 400 MHz) : delta (ppm) = 3.90(s, 3H), 6.85(s, 1H), 8.14(s, 1H)

The synthetic route of 72141-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1679003; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1167056-96-3 ,Some common heterocyclic compound, 1167056-96-3, molecular formula is C7H4BrClN2, 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 a solution of compound 221.4 (l . lg, 7.2mmol, l .Oeq) in dimethylformamide (20mL) at 0C, sodium hydride (0.5mL, 10.8mmol, 1.5eq) was added. Reaction mixture was stirred at 0C for 20min. Then, ethyl iodide (1.6mL, 10.8mmol, 1.5eq) was added. Reaction mixture was stirred at room temperature for 3h. After completion of the reaction, the reaction mixture was transferred into water to obtain the precipitate which was filtered, washed with water and dried well under vacuum to obtain 221.5. (0.9g, 12.91%). MS(ES): m/z 260.37 [M]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1167056-96-3, its application will become more common.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (401 pag.)WO2018/71794; (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.866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, molecular weight is 299.05, as common compound, the synthetic route is as follows.SDS of cas: 866775-18-0

A mixture comprising 3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A step 4) (300 mg, 1.003 mmol), N,N-dimethylprop-2-yn-1- amine (0.1 19 ml, 1.104 mmol) and copper(l) iodide (3.82 mg, 0.020 mmol) in 1 ,4- dioxane (1.500 ml) under nitrogen was treated with triethylamine (1.818 ml, 13.04 mmol) followed by Pd(PPh3)2CI2 (14.08 mg, 0.020 mmol) and stirred at 100C for 15 minutes. A further portion of Pd(PPh3)2CI2 (14.08 mg, 0.020 mmol) was added and stirring continued at 100C for 15 minutes. The mixture was poured into water and extracted with EtOAc. The organic portion was separated and washed with water, brine and dried using a phase separating column. The mixture was acidified to pH1 using 1 M HCI and the aqueous portion was separated and basified to pH7 using saturated sodium bicarbonate solution. The mixture was extracted with EtOAc and the combined organic extracts were washed with brine and dried using a phase separating column. The solvent was removed under reduced pressure to afford the title compound; LC-MS Rt = 0.51 min [M+H]+ 302.4 ; Method 2minl_owpH.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866775-18-0, Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren, Mark; WO2013/38381; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 688782-02-7, 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. 688782-02-7, name is 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7ClN2, 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 4-chloro-3-methyl-lH-pyrrolo[2,3-b]pyridine (1.1 g, 6.6 mmol) in Nu,Nu’- dimethylformamide (20 mL) was added NaH (166 mg, 6.93 mmol) at 0 C. The mixture was stirred at room temperature for 30 minutes and benzenesulfonyl chloride ( 1.2 g, 6.6 mmol) was added. After 2 hours, the reaction was complete and was partitioned between water and ethyl acetate. The organic phase was concentrated and was purified by flash chromatography on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate to provide the title compound. LC/MS m/z 307 (M+H)+.

According to the analysis of related databases, 688782-02-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem