Day: June 10, 2021

Electric Literature of 1620-77-5, 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. 1620-77-5, name is 5-Methylpicolinonitrile. A new synthetic method of this compound is introduced below.

Synthesis Example 1 Ethyl 5-methylpyridine-2-carboxylate STR24 200 ml of ethanol and 100 ml (1.88 mol) of concentrated sulfuric acid were added to 55.5 g of 5-methylpyridine-2-carbonitrile to form a homogeneous solution, followed by heating under reflux for 2 days. The reaction liquid was gradually poured into a saturated aqueous solution of sodium hydrogencarbonate under cooling with ice to neutralize the sulfuric acid, followed by extraction with dichloromethane. The organic layer was washed with a saturated aqueous solution of common salt and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in a reduced pressure to give 78.1 g of a brown oil of the title compound as the crude product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1620-77-5, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US5789403; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1628-89-3, Adding some certain compound to certain chemical reactions, such as: 1628-89-3, name is 2-Methoxypyridine,molecular formula is C6H7NO, 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 1628-89-3.

A: 2 mol of 6-methoxypyridine and 700 ml of a 22percent potassium chloride solution were added to the reaction vessel.1.2L mass fraction of 26percent heptane solution, control solution temperature to 15 ° C,Adding an aqueous solution, 6 mol of aluminum isopropoxide, controlling the stirring speed of 370 rpm, and continuing the reaction for 120 min; B: Then, 6 mol of antimony trichloride powder was added, the temperature was controlled at 26 ° C, the reaction was continued for 3 h, then the temperature was lowered to 8 ° C, allowed to stand for 50 min, and the solution was layered.The oil layer was separated and washed 5 times with a 15percent sodium sulfate solution.The solution was washed 8 times with a mass fraction of 77percent in xylene and recrystallized from a cyclohexene solution having a mass fraction of 86percent.The dehydrating agent was dehydrated with anhydrous sodium sulfate to obtain 216.038 g of the obtained N-methylpyridin-2-one, and the yield was 99.1percent.

According to the analysis of related databases, 1628-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Kadifu Technology Co., Ltd.; Liao Runai; (4 pag.)CN108239022; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1188477-11-3, 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. 1188477-11-3, name is tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate. A new synthetic method of this compound is introduced below.

To a mixture of tert-butyl ((5-bromopyridin-2-yl)methyl)carbamate (2.2 g, 7.7 mmol) in 1,4-dioxone (4 mL) was added a solution of HCl in 1,4-dioxane (20 mL, 60 mmol, 3 M HCl in 1,4-dioxane). The mixture was stirred at 28C for 2 hr then concentrated to dryness to give the crude product (2.2 g crude) as yellow solid which was directly used in the next step without further purification. LC-MS: m/z 186,188 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1188477-11-3, tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; SPERO THERAPEUTICS, INC.; ZAHLER, Robert; (262 pag.)WO2016/112088; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 62150-45-2 , The common heterocyclic compound, 62150-45-2, name is 4-Bromopyridine-2-carbonitrile, molecular formula is C6H3BrN2, 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.

Step 1. 4-Bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine 4-Bromopyridine-2-carbonitrile (1.0 g, 5.5 mmol, Synthonix) in MeOH (10 mL) was treated with sodium methoxide (25 wt percent in MeOH, 0.095 mL, 0.47 mmol) and the reaction was stirred for 1 hour. Ammonium chloride (0.37 g, 6.9 mmol) was added and the reaction was stirred for 4 days. Solvent was then removed in vacuo. Water (4 mL) and EtOAc (6 mL) were added, the mixture was saturated with solid NaCl, and the mixture was stirred overnight. The solid product was isolated by filtration and dried at 40° C. under vacuum overnight. The product was used below without further purification. To 4-bromopyridine-2-carboximidamide (0.50 g, 2.5 mmol) in DMF (5 mL) was added K2CO3 (0.52 g, 3.7 mmol) and 3-bromo-2-butanone (0.24 mL, 3.2 mmol). The reaction was stirred for 4 days. The reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with two further portions of EtOAc. The combined organic extracts were washed sequentially with water and saturated NaCl solution. The organic solution was dried over Na2SO4, filtered, and concentrated. The crude product was triturated with methyl tert-butyl ether (MTBE, 2 mL) and the solid product was isolated by filtration and dried under vacuum at 40° C. for 3 hours. Yield: 372 mg, 59percent. LCMS (M+H)+: 252.0/254.0.

The synthetic route of 62150-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Sparks, Richard B.; Shepard, Stacey; Combs, Andrew P.; Buesking, Andrew W.; Shao, Lixin; Wang, Haisheng; Falahatpisheh, Nikoo; (158 pag.)US2017/190689; (2017); 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 5470-70-2, name is Methyl 6-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step 1: Intermediate 31-b [0181] To a solution of methyl 6-methylnicotinate 31-a (20.10 g, 133 mmol) in THF (90 ml) cooled to 0° C. was added drop wise a 1.0 M solution of LiAlH4 in THF (100 ml, 100 mmol) and the reaction was then stirred at 0° C. for 1 hour. Water (3.8 ml) was slowly added, followed by 15percent NaOH (3.5 ml) and water (11.4 ml) and the mixture was stirred at room temperature for 1 hour. The reaction was filtered over celite and volatiles were removed in vacuo to provide intermediate 31-b as a yellow oil.

With the rapid development of chemical substances, we look forward to future research findings about 5470-70-2.

Reference:
Patent; Pharmascience, Inc.; Laurent, Alain; Rose, Yannick; Jaquith, James B.; US2015/191473; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1214334-70-9, 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.1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid, molecular formula is C7H6BrNO3, molecular weight is 232.0314, as common compound, the synthetic route is as follows.

To a solution of 5-bromo-6-methoxy picolinicacid1 (1.5 g, 0.00646 mol) in DMF (15mL, 10 vol), cooledto 0oC Na2CO3 (685 mg, 0.00646 mol) and MeI (0.834 mL,0.0129 mol) were added and the mixture was stirred for 16hat room temperature. Water was added, extracted with ethylacetate, concentrated under reduced pressure to obtain 5-bromo-6-methoxy-pyridine-2-carboxylic acid methyl ester(1.5 g, 0.00609 mol) in EtOH (15mL), NH2NH2.H2O (1.21 g,0.0243 mol) was added and the mixture was stirred for 3h at70oC, cooled to room temperature, solvents were evaporated,water (15mL) was added, filtered the reaction mass, to givepure compound 2.

Statistics shows that 1214334-70-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-6-methoxypicolinic acid.

Reference:
Article; Namani, Vasu; Goud, B. Bharath Kumar; Kumari, Y. Bharathi; Kumbham, Ramesh; Letters in Organic Chemistry; vol. 13; 4; (2016); p. 249 – 254;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 630120-99-9, 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.630120-99-9, name is 5-(Benzyloxy)-2-bromopyridine, molecular formula is C12H10BrNO, molecular weight is 264.1179, as common compound, the synthetic route is as follows.

To a solution of 5-(benzyloxy)-2-bromopyridine (200 mg, 0.757 mmol), methanamine (70.6 mg, 2.272 mmol) and sodium 2-methylpropan-2-olate (437 mg, 4.54 mmol) in THF (5 mL) was added Pd2dba3 (69.3 mg, 0.076 mmol) and dicyclohexyl(2?,4?,6?-triisopropyl-[1,1?-biphenyl]-2-yl)phosphine (36.1 mg, 0.076 mmol). The reaction mixture was stirred at 60 C. for 15 h. The mixture was cooled and diluted with water (10 mL). After the mixture was extracted with EtOAc (10 mL×3), the combined organic fractions were washed with water (20 mL×3), dried (anhydrous Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by prep-TLC (1/1 petroleum ether/EtOAc) to give the title compound. MS: 215 (M+1).

Statistics shows that 630120-99-9 is playing an increasingly important role. we look forward to future research findings about 5-(Benzyloxy)-2-bromopyridine.

Reference:
Patent; BAO, JIANMING; GAO, XIAOLEI; KNOWLES, SANDRA L.; LI, I, CHUNSING; LO, MICHAEL MAN-CHU; MAZZOLA, Jr., ROBERT D.; ONDEYKA, DEBRA L.; STAMFORD, ANDREW W.; ZHANG, FENGQI; (214 pag.)US2017/183342; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84249-14-9, 2-Amino-4-bromopyridine, 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 2-Amino-4-bromopyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Amino-4-bromopyridine

Step 1: N-(4-bromopyridin-2-yl)acetamide To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol). The reaction mixture was allowed to stir at 140 C. for 3 h and then allowed to cool to rt. Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NH4OH. The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g, 89%) as a white solid.

The synthetic route of 84249-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1060811-62-2, 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.1060811-62-2, name is 4,6-Dichloronicotinaldehyde, molecular formula is C6H3Cl2NO, molecular weight is 176, as common compound, the synthetic route is as follows.

To a reaction vessel containing a mixture of 4,6-dichloronicotinaldehyde (300 g, 1.7 mol) in 1,4- dioxane (1200 mL) was added hydrazine (50%> in water)(360 mL, 3.6 mol). The reaction vessel was sealed and heated at 150 C over 18 h. The mixture was cooled to room temperature, concentrated in vacuo, poured over water and filtered. The filter cake was washed with 20%> EtOAc in hexanes and dried to afford 6-chloro-lH-pyrazolo[4,3-c]pyridine (101.4 g, 38 %>) as a light-yellow solid. LCMS (ESI) [M+H]+ = 154.

The chemical industry reduces the impact on the environment during synthesis 1060811-62-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; DIEDERICH, Francois; DOTSON, Jennafer; HANAN, Emily; HEFFRON, Timothy; LAINCHBURY, Michael; HEALD, Robert; SEWARD, Eileen M.; WO2014/210354; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 74420-15-8 ,Some common heterocyclic compound, 74420-15-8, molecular formula is C7H5BrN2, 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.

[0193] In a microwave tube was placed ethyl 2-bromothiazole-4-carboxylate (944 mg, 4 mmol), 3-bromo-1H-pyrrolo[2,3-blpyridine (867 mg, 4.40 mmol), and K2C03 (663 mg, 4.80 mmol). The tube was sealed and DMSO (7.5 ml) was added. The mixture was heated at 150C for 3 h. The mixture was poured into EtOAc/H20 (30 mL/30 mL). The organic was dried (Na2504) and filtered. After removal of the solvent, the product was purified (twice) by silica gel chromatography using 10-20% EtOAc/hexane as the eluent to give ethyl 2-(3- bromo- 1 H-pyrrolo[2,3 -blpyridin- 1 -yl)thiazole-4-carboxylate (587 mg, 1.667 mmol, 41.7% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74420-15-8, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem