Month: April 2022

Electric Literature of 1256561-65-5, 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. 1256561-65-5, name is 3-(Bromomethyl)-5-fluoropyridine hydrobromide. A new synthetic method of this compound is introduced below.

A mixture of 3-(bromomethyl)-5-fluoropyridine hydrobromide (3.4 mmol), 6-methyl- 2-sulfanylpyrimidin-4-ol (370 mg, 2.6 mmol), and triethylamine (1.7 mL, 12.0 mmol) in absolute ethanol (40 mL) was stirred at room temperature overnight. The solid material was removed by filtration. The filtrate was recovered, evaporated, co- evaporated with EtOAc (20 mL), and then dried in vacuo. The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (1 x 20 mL) and diethyl ether (2 x 20 mL), and then dried in vacuo, affording the 2-{[(5-fluoropyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (200 mg, 23% yield); 1H NMR (400 MHz, OMS0-d6): delta 2.21 (s, 3H), 4.41 (s, 2H), 6.02 (s (br), IH), 7. 80 (m, IH), 8.05 (dd, IH, / = 2.0 Hz, 7.6 Hz), 8.46 (d, IH, J = 2.7 Hz), 8.54 (t, IH, J = 1.6 Hz); M+ 252. The product was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1256561-65-5, its application will become more common.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); 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.98273-79-1, name is Methyl 3-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Quality Control of Methyl 3-chloroisonicotinate

A solution of 1-(bromomethyl)-4-(methylsulfanyl)benzene (prepared according to D. D. M. Wayner, D. R. Arnold, Can J. Chem., 1984, 62, 1164) (2.54 g, 11.7 mmol) in THF (10 mL) was added dropwise to a slurry of Riecke Zinc in THF (22.8 mL of a commercial suspension [5g Zn/100 mL], 17.5 mmol) under nitrogen. During this time the temperature rose steadily to 35C. After allowing the black slurry to cool to room temperature over 30 min bis(triphenylphosphine)nickel (II) chloride (762 mg, 1.17 mmol) was added followed by a solution of methyl 3-chloroisonicotinate (prepared according to J. Epsztajn, M. W. Plotka, A. Grabowska, Synth. Commun., 1997, 27, 1075) (1.0 g, 5.83 mmol) in THF (10 mL), dropwise, taking care to keep the temperature below 30C. After the addition was complete the reaction was allowed to cool to room temperature over 1 h before being quenched by the addition of sat. NH4Cl (aq) (20 mL) while cooling with an ice bath. The mixture was filtered through Celite ), washing well with EtOAc (3 x 20 mL), the organic layer was separated, dried (MgS04) and evaporated to give a brown oil. The residue was purified by column chromatography [SiO2; EtOAc:pentane, 1:3 increasing polarity to EtOAc:pentane, 1:1 and then to (EtOAc:MeOH:NH40H, 95:5:0.5):pentane, 1:1] to give the title compound as an orange oil; & delta H (CDCl3, 400 MHz) 2.43 (3H, s), 3.82 (3H, s), 4.30 (2H, s), 7.05 (2H, d), 7.18 (2H, d), 7.67 (1H, br), 8.59 (2H, br); MS m/z (TS+) 274 (MH+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Limited; Pfizer Inc.; WO2004/16593; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 67058-77-9, Adding some certain compound to certain chemical reactions, such as: 67058-77-9, name is 3-Nitro-1H-pyrrolo[2,3-c]pyridine,molecular formula is C7H5N3O2, 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 67058-77-9.

To a solution of 3-nitro-1H-pyrrolo[2,3-c]pyridine (200 mg, 1.23 mmol) in MeOH (20 mL) was added 10% Pd/C (130 mg, 0.12 mmol). After stirred at balloon hydrogen atmosphere for 2 hrs, the mixture was filtered. The filtrate was evaporated in vacuum to give 1H- pyrrolo[2,3-c]pyridin-3-amineas a crude product which was used for next step without further purification.

According to the analysis of related databases, 67058-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 184368-74-9, name is 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C12H19NO4

To a solution of 1-tert-butyl 4-methyl 3,6-dihydro-2H-pyridine-l,4-dicarboxylate (500 mg, 2.07 mmol) in toluene (2.5 mL) was added tetrabutylammoniumbromide (33 mg, 0.10 mmol) under N2, then [bromo(difluoro)methyl]-trimethyl-silane (842 mg, 4.14 mmol) was added drop-wise under N2. The reaction mixture was heated at 110 C and stirred for 16 h in a sealed tube. The residue was filtered and concentrated under reduced pressure to provide the title compound (700 mg) as a brown oil, which was used in the next step without further purification. LC-MS: m/z = 192.1 [M+H]+.

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, 184368-74-9, 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate.

Reference:
Patent; DENALI THERAPEUTICS INC.; DE VICENTE FIDALGO, Javier; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian; FRANCINI, Cinzia Maria; HALE, Christopher R.H.; HU, Cheng; LESLIE, Colin Philip; OSIPOV, Maksim; SERRA, Elena; SWEENEY, Zachary K.; THOTTUMKARA, Arun; (226 pag.)WO2018/213632; (2018); 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

Related Products of 1064783-29-4 ,Some common heterocyclic compound, 1064783-29-4, molecular formula is C5H2ClFN2O2, 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.

5-Chloro-3-fluoro-2-nitropyridin (190.0 mg, 1.08 mmol) and hydrazine monohydrate (80.0 muL, 1.61 mmol) were dissolved in EtOH (3.0 mL) and the mixture was stirred at room temperature for 2 hours. Et2O was added thereto to form a solid, and the formed solid was filtered to obtain orange solid compound of 5-chloro-3-hydrazinyl-2-nitropyridine (170.0 mg, 84%). [1074] 1H-NMR (300 MHz, DMSO-d6); delta: 9.06 (brs, 1H), 8.10 (m, 1H), 7.76 (d, 1H, J=2.4 Hz)

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. 1064783-29-4, 5-Chloro-3-fluoro-2-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; C&C RESEARCH LABORATORIES; Ho, Pil Su; Yoon, Dong Oh; Han, Sun Young; Lee, Won Il; Kim, Jung Sook; Park, Woul Seong; Ahn, Sung Oh; Kim, Hye Jung; US2014/315888; (2014); A1;,
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

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.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.Application In Synthesis of tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate

To a stirred solution of tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (10 g, 29.21 mmol) in 1,4-dioxane (50mL), 4N HCI solution in dioxane (100 mL, 10V) was added and the mixture was stirred 4 h at rt. The white precipitate formed was filtered and residue was washed with diethyl ether (25 mL) to afford the title compound. Yield: 95.2% (9 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 10.05 (br s, 2H), 8.21 (d, J = 2.4 Hz, 1 H), 7.82 (dd, J = 9.2, 2.4 Hz, 1 H), 6.99 (d, J = 9.2 Hz, 1 H), 3.80-3.77 (m, 4H), 3.33-3.13 (m, 4H). LCMS: (Method A) 243.9 (M +2H), Rt. 1.69 min, 99.3 % (Max).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); 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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C19H16BrNO2

To a stirred solution of 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzo[d]thiazole (36-2) (1.1 g, 3.99 mmol) and 2,6-bis(benzyloxy)-3-bromopyridine 25-1 (1.9 g, 5.13 mmol) in a sealed tube, in Dioxane (20 mL ) and Water (2 mL ), was added K3PO4 (2.1 g, 9.12mmol) and the solution was degassed for 10 min. PdCl2(dppf)-DCM (0.400 g, 489 mumol) was added and again the solution was degassed for 5 min. After degassing completion, the sealed tube was closed with a teflon cap and the reaction mixture was stirred at 80c for 16 h. After reaction completion, as checked by TLC, the reaction mixture was filtered through celite. The organic layer was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography eluted with 5 to 20 % ethyl acetate in hexane to provide 5- (2,6-Bis-benzyloxy-pyridin-3-yl)-2-methyl-benzothiazole (36-3) (1.0 g, 2.28 mmol, 57% yield). LC MS: ES+ 439.3.

The synthetic route of 16727-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
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