Tag: M.W:200-300

Reference of 204378-41-6 ,Some common heterocyclic compound, 204378-41-6, molecular formula is C8H8ClNO3, 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 solution of 6-chloro-4-methoxy-2-carboxylic acid methyl ester (2.63 g, 13.0 mmol) in dioxane (150 mL) is degassed and put under argon before Pd(dppf) (109 mg, 133 mumol) is added. To this mixture, 1-ethyl-propyl zink bromide (50 mL of a 0.5 M solution in THF, 25.0 mmol) is added dropwise. The mixture is stirred at 76°C for 15 h. The mixture is cooled to rt, diluted with water and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with a gradient of EA in heptane to give 6-(1-ethyl-propyl)-4-methoxy-pyridine-2- carboxylic acid methyl ester (450 mg) as a pale yellow oil; LC-MS**: tR = 0.46 min; [M+1]+ = 238.34.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,204378-41-6, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/109872; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 179687-79-7, 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 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of the relevant nitro derivative (1a-d) (1 equiv., 3 mmol), reduced iron powder (3 equiv., 9 mmol, 0.5 g) and NH4Cl (9 equiv., 27 mmol, 1.44 g) in 70% EtOH/H2O (20 mL) was heated at reflux temperature (70 oC) for 2 hours. The reaction mixture was filtered over a Celite pad to remove the insoluble iron oxides. The filtrate was evaporated under vacuum to residue, to which EtOAc was added, then the resulting suspension was filtered to remove the inorganic salts. The filtrate was dried over anhydrous Na2SO4 and evaporated under vacuum affording crystals of the designated compounds (2a-d), then the crystals were washed with cold n-hexane. [2-4]

According to the analysis of related databases, 179687-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Milik, Sandra N.; Abdel-Aziz, Amal Kamal; Lasheen, Deena S.; Serya, Rabah A.T.; Minucci, Saverio; Abouzid, Khaled A.M.; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 316 – 336;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 878197-68-3 ,Some common heterocyclic compound, 878197-68-3, molecular formula is C8H5BrN2O, 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 5-bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (1.42 g, 6.31 mmol) in methyl alcohol (30 mL) cooled to O0C was added sodium borohydride (286 mg, 7.57 mmol). The mixture was stirred at room temperature for 4 hours, quenched with water, and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate and concentrated to give 0.6 g (42% yield) 5-bromoimidazo[1 ,2- a]pyridin-2-yl)methanol as an orange solid. 1H-NMR (CDCI3): delta 7.76 (s, 1 H), 7.55 (d, 1 H), 7.09 (m, 1 H), 7.03 (dd, 1 H), 4.87 (s, 2H); MS m/z 227 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,878197-68-3, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/36816; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55404-31-4, 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.55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine, molecular formula is C6H5BrClN, molecular weight is 206.47, as common compound, the synthetic route is as follows.

3-Bromo-2-(4-methoxybenzyloxy)-4-methylpyridine 3-bromo-2-(4-methoxybenzyloxy)-4-methylpyridine was prepared by the procedure described in J. Med. Chem., 2008, 51, 3065. A pressure vessel was charged with anhydrous THF (25 ml) and sodium hydride (1.44 g, 36.18 mmol, 60% dispersion). To this stirred mixture was added portionwise a solution of 4-methoxybenzyl alcohol (5.0 g, 36.18 mmol) in anhydrous THF (15 ml). After addition was complete, the mixture was stirred at room temperature for 30 minutes and a solution of 3-bromo-2-chloro-4-picoline (4.97 g, 24.08 mmol) in anhydrous THF (15 ml) was added. The vessel was sealed and the reaction mixture was heated at 75 C. for 6 hours. Upon cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with water, sat’d NaCl(aq.), dried over MgSO4, filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 4:1 hexanes:EtOAc) gave the title compound as a clear oil which crystallized on standing (6.71 g, 90%).

The chemical industry reduces the impact on the environment during synthesis 55404-31-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Allergan, Inc.; Wurster, Julie; Yee, Richard; Hull III, Clarence Eugene; Malone, Thomas C.; (39 pag.)US2016/96832; (2016); 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 947179-03-5, name is Ethyl 4-bromo-6-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 947179-03-5

Step 5: 4-Bromo-6-methyl-pyridine-2-carboxylic acid (4-methyl-thiazol-2-yl)-amide To a solution of 3.72 g (32.6 mmol) of 2-Amino-4-methylthiazole in 40 ml of dry dioxane were added dropwise 15.9 ml (31.8 mmol, 4.0 equiv.) of a 2M solution of trimethylaluminium in hexane. The solution was stirred for 30 min at room temperature. Then a solution of 1.94 g (7.95 mmol) of 4-Bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester in 6 ml of dry dioxane was added dropwise and the reaction was heated to 100 C. for 1.5 h. The reaction was quenched by cautious addition of 2.5 ml of water. Then approximately 10 g of anhydrous sodium sulfate were added to bind the water and the mixture was stirred vigorously for 5 min. The mixture was diluted by addition of 20 ml of methylene chloride and filtered over Speedex filteraid which was washed with methylene chloride. The filtrate was concentrated in vaccuo and the residue was purified by flash chromatography (heptane/ethyl acetate 4:1) to yield the title compound (1.95 g, 79%) as a yellow solid, MS (ISP): m/e=312.0, 314.0 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 947179-03-5.

Reference:
Patent; Jaeschke, Georg; Spooren, Will; Vieira, Eric; US2007/197553; (2007); 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. 1073159-75-7, name is N-(3-(Aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide acetate, molecular formula is C10H17N3O4S, 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: N-(3-(Aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide acetate

Step 2. A solution of tert-butanol (20.0 mL), DCE (20.0 mL) and DIEA (3.13 mL, 18.0 mmol) was treated with C8 (5.60 g, 15.0 mmol) and B5 (5.02 g, 15.0 mmol), and the resulting mixture was stirred at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was cooled to 25 C. and concentrated. The resultant residue was partitioned between EtOAc and 1 N sodium hydroxide, and the organic phase was collected. The aqueous layer was extracted with EtOAc, and the combined organic phases were dried over MgSO4 and filtered. The resultant filtrate was concentrated under reduced pressure, and the resultant residue was triturated with hot EtOAc to provide 9 as a white solid. Yield: 7.83 grams, 95%. LC/MS (standard) 250=3.0 min., m/z 553.6 (MH+). HPLC (FAK1) 250=8.14 min. 1H NMR (d6-DMSO) : 9.75 (bs, 1H), 8.44 (d, J=5.2 Hz., 1H), 8.29 (s, 1H), 8.05 (bs, 1H), 7.82 (d, J=7.8 Hz., 1H), 7.60 (t, J=5.7 Hz., 1H), 7.44-7.40 (m, 2H), 7.17 (t, J=5.7 Hz, 1H), 4.82 (d, J=5.7 Hz., 2H), 3.16 (s, 3H), 3.13 (s, 3H), 1.51 (s, 9H) ppm. FAK IC50: 0.0006 muM

With the rapid development of chemical substances, we look forward to future research findings about 1073159-75-7.

Reference:
Patent; Pfizer Inc.; US2009/54395; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886364-94-9, 5-Bromo-4-methylpicolinaldehyde, 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: C7H6BrNO, blongs to pyridine-derivatives compound. COA of Formula: C7H6BrNO

To a solution of ethylene glycol (310 mg, 5.00 mmol, 280 pL, 2.00 equiv), 5-bromo-4- methyl-pyridine-2-carbaldehyde (500 mg, 2.50 mmol, 1.00 equiv) in toluene (20.0 mL) was added / oluenesul fonic acid (47.6 mg, 250 pmol, 0.10 equiv). The mixture was stirred at 110 C for 12 h and was subsequently concentrated in vacuo to give a residue. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate = 1/0 to 5: 1) to afford 5-bromo- 2-(l, 3-dioxolan-2-yl)-4-methylpyridine (320 mg, 1.24 mmol, 49.6% yield) as a colorless oil. 1H NMR (400MHz, CDCI3) d = 8.64 (s, 1H), 7.42 (s, 1H), 5.80 (s, 1H), 4.19 – 4.14 (m, 2H), 4.10 – 4.05 (m, 2H), 2.42 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886364-94-9, 5-Bromo-4-methylpicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 90145-48-5, Adding some certain compound to certain chemical reactions, such as: 90145-48-5, name is 5-Bromopyridine-2-carboxamide,molecular formula is C6H5BrN2O, 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 90145-48-5.

Step 1 5-Triotabutylstannanyl-pyriotadiotane-2-carboxyhc acid amide[00294] A degassed mixture of 5-bromo-py?dme-2-carboxylic acid (0 2g, lmmol), t?butyltm(1 16g, 2mmol) and PdCl2(PPh3)2 (0 07g, 0 lmmol) in DMF (4mL) is stirred at 1150C Additional 20% of PdCl2(PPh3)2 (0 14g, 0 2mmol) is added and the reaction stirred for 24 hours The reaction mixture is partitioned between EtOAc and water, the organic layer is washed with water (4x), d?ed over MgSO4, filtered and concentrated in vacuo The crude is purified by silica gel column chromatography eluting with 9 1 petroleum ether-ethyl acetate to afford the title compound (O 132 mg, 32%)

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. 90145-48-5, 5-Bromopyridine-2-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 880870-13-3

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mE) was purged with nitrogen for 15 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, succes30 sively. The resulting suspension was stirred at 95 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to providethe crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate/hexanes to afford theproduct.?H NMR (500 MHz, DMSO-d5), oe 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); EC/MS (M+1)=169.

The synthetic route of 880870-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Walsh, Shawn P.; Pasternak, Alexander; Shi, Zhi-Cai; Cato, Brian; Kim, Esther Y.; (32 pag.)US9493474; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 947249-13-0, 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.947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, molecular formula is C6H5BrF2N2O, molecular weight is 239.02, as common compound, the synthetic route is as follows.

A mixture of 5-bromo-3-(difluoromethoxy)pyridine-2-amine (88 mg, 0.37 mmol), bis(pinacolato)diboron (102 mg, 0.40 mmol), potassium acetate (0.215 mg, 2.2 mmol), and Pd(dppf)-CH2Cl2 (30 mg, 0.037 mmol) in dry dioxane (2.0 mL) was sparged with argon, and heated at 120 C. for 30 min. After cooling to rt, the reaction mixture was centrifuged and the supernatant decanted, and used in the next step without further purification: LCMS (m/z, MH+, boronic acid): 205.0, tR=0.27 min.

Statistics shows that 947249-13-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-(difluoromethoxy)pyridin-2-amine.

Reference:
Patent; Huang, Zilin; Jin, Jeff; Machajewski, Timothy; Antonios-McCrea, William R.; McKenna, Maureen; Poon, Daniel; Renhowe, Paul A.; Sendzik, Martin; Shafer, Cynthia; Smith, Aaron; Xu, Yongjin; Zhang, Qiong; Chen, Zheng; US2013/210818; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem