Pyridine-derivatives

Application of 73290-22-9 , The common heterocyclic compound, 73290-22-9, name is 2-Bromo-5-iodopyridine, molecular formula is C5H3BrIN, 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.

1-Ethynylferrocene (500 mg, 2.38 mmol) was dissolved in THF/TEA (20 mL, 1:1 v/v) and the solutionwas degassed (argon) for 10 minutes. 2-Bromo-5-iodopyridine (614 mg, 2.16 mmol),[Pd(CH3CN)2Cl2]2 (38 mg, 0.054 mmol) and CuI (41 mg, 0.216 mmol) were added and the mixture wasstirred at RT under inert atmosphere overnight. The reaction mixture was diluted with CH2Cl2 (50mL) and washed with EDTA/NH4OH(aq) (0.1 M, 100 mL). The organic layer was separated and theaqueous layer was extracted with CH2Cl2 (2 x 50 mL). The combined organic layers were washed withbrine (80 mL), dried over Na2SO4, filtered, and the solvent was removed under reduced pressure.Purification by column chromatography (silica gel, gradient 1:1 CH2Cl2/petrol to CH2Cl2 to 19:1CH2Cl2/acetone) gave the product as an orange crystalline solid upon removal of solvent. Yield: 0.776g, 98%.

The synthetic route of 73290-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Findlay, James A.; Barnsley, Jonathan E.; Gordon, Keith C.; Crowley, James D.; Molecules; vol. 23; 8; (2018);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 178876-82-9, name is Methyl 6-amino-5-bromopicolinate. A new synthetic method of this compound is introduced below., Quality Control of Methyl 6-amino-5-bromopicolinate

Preparation 4; Preparation of 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxaldehydea) Methyl 3-oxo-3,4-dihydro-2H-pyrido[3.2-b][1,4]thiazine-6-carboxylateA solution of ethyl 2-mercaptoacetate (1.473 mL) in DMF (48 mL) was ice-cooled and treated with sodium hydride (540 mg of a 60% dispersion in oil). After 1 hour methyl 6-amino-5-bromopyridine-2-carboxylate (3 g) (T. R. Kelly and F. Lang, J. Org. Chem. 61, 1996, 4623-4633) was added and the mixture stirred for 16 hours at room temperature. The solution was diluted with EtOAc (1 litre), washed with water (3×300 mL), dried and evaporated to about 10 mL. The white solid was filtered off and washed with a little EtOAc to give the ester (0.95 g); MS (APCl-) m/z223 ([M-H]-, 100%).

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, 178876-82-9, Methyl 6-amino-5-bromopicolinate.

Reference:
Patent; Glaxo Group Limited; US2008/194547; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, 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, HPLC of Formula: C14H20N4O4, blongs to pyridine-derivatives compound. HPLC of Formula: C14H20N4O4

EXAMPLE 103C ierf-butyl 4-(6-aminopyridin-3-yl)piperazine-l -carboxy late To a suspension of EXAMPLE 103B (4.5 g, 14.6 mmol) in methanol (100 mL) was added Raney -Nickel (450 mg) and the mixture was stirred at ambient temperature under hydrogen for 4 hours. The catalyst was filtered off and the filtrate was concentrated to give the title compound, which was used in the next step without further purification.

The synthetic route of 571189-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1382486-27-2 ,Some common heterocyclic compound, 1382486-27-2, molecular formula is C10H10BrNO2, 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 stirred solution of l-(5-bromopyridin-2-yl)cyclobutanecarboxylic acid (16.9 g, 66.0 mmol) in i-BuOH (30 mL) was added TEA (17.5 mL, 125 mmol) and DPPA (23.6 g, 86 mmol) at RT. After the addition was finished, the reaction was stirred at 85 C under nitrogen for 18 h. After 18 h the solvent was concentrated in vacuo. The residue was purified via column chromatography (Petroleum ether/ EtOAc =10: 1-2: 1) to afford tert-butyl (l-(5-bromopyridin-2- yl)cyclobutyl)carbamate. MS ESI calc’d. [M + H]+ 327, found 327.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1382486-27-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WHITE, Catherine M.; ACHAB, Abdelghani; BHARATHAN, Indu T.; FRADERA, Xavier; HAN, Yongxin; LI, Derun; LIM, Jongwon; LIU, Kun; MCGOWAN, Meredeth Ann; SCIAMMETTA, Nunzio; YU, Wensheng; ZHANG, Hongjun; ZHOU, Hua; (107 pag.)WO2019/74749; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 68618-36-0, 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 68618-36-0, name is 3-Bromo-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-1H-pyrazolo[3,4-b]pyridine (200 mg, 1.010 mmol), zinc cyanide (1.0 eq., 121.0 mg, 1.010 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.04 eq., 38.1 mg, 0.040 mmol), 1,1?-bis(diphenylphosphino)feffocene (0.08 eq., 46.6 mg, 0.08 1 mmol) and zinc (0.24 eq., 15.8 mg, 0.242 mmol) were dissolved in degassed N,N-dimethylacetamide (5.0 mL) under inert atmosphere. The reaction was heated to 120 C for 5 hours. The reaction was then diluted withaqueous saturated sodium bicarbonate and extracted 2 times with dichloromethane. The organics were combined, washed with brine, dried with sodium sulfate and concentrated under vacuum. The crude material was crashed out in diethyl ether to afford 93 mg of the title compound (64 %).

According to the analysis of related databases, 68618-36-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1013648-04-8, 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. 1013648-04-8, name is Methyl 2,6-dichloro-4-methylnicotinate, molecular formula is C8H7Cl2NO2, 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 250 ml flask were added methyl 2,6-dichloro-4-methylnicotinate (4.24 g, 19.268 mmol), N-bromosuccinimide (4.1 g, 23.036 mmol), azobisisobutyronitrile (160 mg, 0.974 mmol) and 50 ml of carbon tetrachloride. The reaction mixture was stirred at 85 C. overnight. The reaction mixture was concentrated to remove carbon tetrachloride, and 50 ml of ethyl acetate was added, which was then washed with 50 ml of brine and 50 ml of water successively. The organic phase was dried over anhydrous sodium sulfate, concentrated to give 6.4 g of methyl 4-(bromomethyl)-2,6-dichloronicotinate as an oil, MS m/z (ESI): 300.1[M+H]+.

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 1013648-04-8, Methyl 2,6-dichloro-4-methylnicotinate.

Reference:
Patent; SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO., LTD.; YANGTZE RIVER PHARMACEUTICAL GROUP CO., LTD.; GUO, Shuchun; ZHOU, Fusheng; CHEN, Xiang; ZHAO, Jinzhu; HUANG, Dong; XIE, Jing; QIAO, Changjiang; HE, Wan; ZHANG, Kai; CHEN, Xi; LAN, Jiong; (53 pag.)US2020/48248; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 164666-68-6, 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. 164666-68-6, name is 6-Chloro-2-methylpyridin-3-amine, molecular formula is C6H7ClN2, 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.

Step 2: 6-Chloro-N-isopropyl-2-methylpyridin-3-amine (45). To a stirred solution of 44 (4.81 g, 33.75 mmol) and acetone (2.74 g, 47.2 mmol) in dichloroethane (60 mL) was added NaBH(OAc)3 (10.713 g, 50.53 mmol) and AcOH (3.44 g, 57.2 mmol) at RT. The reaction was stirred for 16 h followed by dilution with IN NaOH. The aqueous solution was extracted with DCM and the organic layer was washed with water, brine, dried over Na2S04 and concentrated to afford 45 (6.16 g, 98%).

According to the analysis of related databases, 164666-68-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; XU, Wei; (106 pag.)WO2017/4608; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-54-9, 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.1122-54-9, name is 4-Acetylpyridine, molecular formula is C7H7NO, molecular weight is 121.14, as common compound, the synthetic route is as follows.

To a mixture of NaH (6.6 g, 165.2 mmol, 60%in mineral oil) in toluene (120 mL) was added dimethyl carbonate (11.2 g, 123.9 mmol) in toluene (40 mL) . Then 1- (pyridin-4-yl) ethanone (5.0 g, 41.3 mmol, 5) in toluene (40 mL) was added dropwise under N 2. The reaction mixture was stirred at 105 for 12 hours. After cooled to RT, the reaction was quenched with 200 mL (water) and HOAc (20 mL) and the mixture was stirred at RT for 20 minutes. Then the mixture was extracted with EtOAc (300 mL*3) . The combined organic layer was dried over Na 2SO 4, filtered and concentrated. The residue was purified by Prep-HPLC (water/acetonitrile = 10%to 90%) to give the title product (3.89 g, 53%, 6) as a brown solid. LC-MS: Rt = 1.20 min, [M+H] + = 180.

The chemical industry reduces the impact on the environment during synthesis 1122-54-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SHANGHAI CHANGCHENGYIYAOKEJI COMPANY LIMITED; XU, Mingyan; (0 pag.)WO2020/1475; (2020); 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.73895-98-4, name is 6-Bromo-4-methylpyridin-2-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.SDS of cas: 73895-98-4

This compound was forwarded to the next step without further purification. To a stirred solution of 6-amino-2-bromo-4-methylpyridine (45.2 g; 0.24 mol) in 100 ml water and 43 g concentrated sulphuric acid at ice-bath temperature was given a solution of sodium nitrite (13.2 g; 0.19 mol) in 20 ml water. After 2 hours the reaction mixture was warmed to 60 C. and stirred for further 60 minutes. After cooling, the mixture was extracted with 200 ml of dichloromethane. The solvent was removed in vacuo and 2-bromo-4-methyl-6-hydroxypyridine (20 g, 56%) was obtained as colourless crystals of melting point 152 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73895-98-4, 6-Bromo-4-methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; American Cyanamid Company; US5840654; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1122-70-9, 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. 1122-70-9, name is 6-Methyl-2-vinylpyridine. A new synthetic method of this compound is introduced below.

Step F: Preparation of 1-[2-(6-Methyl-2-pyridyl)ethyl]-4-(benzofurazan-5-carbonyl)piperidine dihydrochloride 4-(Benzofurazan-5-carbonyl)piperidine hydrochloride (268 mg, 1 mmol), 2-methyl-6-vinylpyridine (286 mg, 2.4 mmol) and sodium acetate (187 mg, 2.3 mmol) in methanol/water (1:1, 4 ml) were heated under reflux for 3 hours, cooled and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluding with CH2 Cl2 /CH3 OH/NH3 (Aq.); 96:4:0.4 to give a light brown solid. This was suspended in ethanol (2 ml) and ethanolic HCl (Ca. 1M, 2 ml) was added. The mixture was stirred at room temperature for 4 hours and the solid was collected and dried in vacuo to give the dihydrochloride as a light brown solid (260 mg. 61%), mp 228-231 C. deltaH(DMSO) 11.1 (1H, br s), 9.05 (1H, s), 8.25 (1H, br m), 8.19 (1H, d, J 9.5 Hz), 7.99 (1H, d, J 9.5 Hz), 7.65 (2H, br m), 4.0-3.1 (10H, m), 2.71 (3H, s), and 2.10 (4H, br m). Elemental analysis for C20 H22 N4 O2.2HCl: Calculated: C, 56.74; H, 5.71; N, 13.23%. Found: C, 56.34; H, 5.80; N, 13.13%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-70-9, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5112824; (1992); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem