Tag: M.W:200-300

Electric Literature of 152684-30-5 ,Some common heterocyclic compound, 152684-30-5, molecular formula is C6H5BrN2O3, 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.

AL 2-Methoxy-3-nitro-5-(4,4,5,5-tetramethyl-L3,2-dioxaborolan-2-yl)pyridine; To a dry flask was added 5-bromo-2-methoxy-3-nitropyridine (1.3 g, 5.0 mmol),4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.6 g, 6.4 mmol), and Pd(dppf)Cl2 (0.2 g, 0.25 mmol). Potassium acetate (1.5 g, 15 mmol) was weighed directly into the flask. The flask was then evacuated and back filled with N2. Anhydrous N,N-dimethylformamide (30 mL) was added and the reaction was heated at 80 0C in an oil bath overnight. The reaction mixture was evaporated to dryness. The residue was dissolved in ethyl acetate (20 mL) and washed with water (20 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting material was purified by silica gel chromatography (eluting with 0-50% ethyl acetate in hexane) to yield the product (0.2 g, 15%). ESI-MS m/z calc. 280.12, found 199.1 (MW[-C6Hio]+l)+. Retention time 0.7 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,152684-30-5, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/141119; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 920979-04-0, 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. 920979-04-0, name is 2-Iodo-6-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4F3IN2, 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.

10.2 (5-Trifluoromethyl)pyrrolo[3,2-b]pyridine-2-carboxylic acid; 0.5 g (1.74 mmol) of 3-amino-2-iodo-6-(trifluoromethyl)pyridine, obtained in Stage 10.1, 0.45 g (5.21 mmol) of pyruvic acid, 0.51 mL (5.21 mmol) of 1,4-diazabicyclo[2.2.2]octane and 10 mL of dry dimethylformamide are introduced, under argon, into a sealed tube. The solution is degassed for some minutes, then 0.19 g (0.87 mmol) of palladium acetate is added, the tube is closed and it is refluxed at 130 C. for 4 hours. The cooled solution is then concentrated at reduced pressure and the residue is taken up in 100 mL of ethyl acetate. The organic phase is extracted successively with 2×50 mL of an aqueous solution of 2N sodium hydroxide. The basic aqueous phases are combined, cooled to 0 C., acidified with additions of hydrochloric acid and then extracted with 4×50 mL of ethyl acetate. These organic phases are combined, washed with 20 mL of a saturated aqueous solution of sodium chloride, dried over sodium sulfate and then concentrated at reduced pressure. We obtain 0.22 g of product, which is used as it is in the next stage.

According to the analysis of related databases, 920979-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2010/41634; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14482-51-0, 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.14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.89, as common compound, the synthetic route is as follows.

NMP (7 mL) was added to a round bottom, placed under nitrogen and cooled to 00C. NaH (1.16 g, 29.1 mmol) was added portionwise followed by the addition of methyl cyanoacetate (1.31 ml, 14.5 mmol) (in 3 mL of NMP) dropwise. After stirring for 30 minutes at 00C, 2- bromo-3,5-dichloropyridine (3.0 g, 13.2 mmol) was added and the reaction was heated to 1300C for 5 hours. The reaction was allowed to cool, poured into ice and extracted twice with ethyl acetate. The ethyl acetate was combined, dried over MgSO4, filtered and concentrated. The amorphous material was crystallized from methanol to afford the desired compound (700 mg, 2.86 mmol, 21.6 % yield) as light brown needles.

Statistics shows that 14482-51-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-3,5-dichloropyridine.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73290-22-9, 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.73290-22-9, name is 2-Bromo-5-iodopyridine, molecular formula is C5H3BrIN, molecular weight is 283.89, as common compound, the synthetic route is as follows.

To a solution of 2-bromo-5-iodopyridine (15 g, 52.8 mmol) in dry THF (300 mL) at -78C was added n-BuLi (2.5 M, 21 mL), and stirred at -78 C for 1 hrs, followed by addition of tert-butyl 3-oxopiperidine-1-carboxylate (10.5 g, 52.8 mmol) in THF. The reaction mixture was stirred at -78 C–6O C for 2 hrs, quenched by NH4C1/H20 and extracted by EA. The organic was dried to give a residue, which was purified by flash chromatography to afford the titlecompound (8.4 g, 45%). MS (ES+) C15HnBrN2O3 requires: 356, found: 357 [M+H].

The chemical industry reduces the impact on the environment during synthesis 73290-22-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BROOIJMANS, Natasja; BRUBAKER, Jason, D.; FLEMING, Paul, E.; HODOUS, Brian, L.; KIM, Joseph, L.; WAETZIG, Josh; WILLIAMS, Brett; WILSON, Douglas; WILSON, Kevin, J.; (347 pag.)WO2017/181117; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 142266-62-4, Adding some certain compound to certain chemical reactions, such as: 142266-62-4, name is 2,5,6-Trichloronicotinamide,molecular formula is C6H3Cl3N2O, 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 142266-62-4.

[0546] Into a 100-mL 3 -necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of 2,5,6-trichloronicotinamide (4.00 g, 17.9 mmol, 1.00 equiv) in DMF (30 mL) and 5-hydroxypentan-2-one (2.00 g, 19.6 mmol, 1.10 equiv). This was followed by the addition of sodium hydride (470 mg, 19.58 mmol, 1.10 equiv) in portions at 0 C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 40 mL of water. The solid was collected by filtration and dried in an oven under reduced pressure. This resulted in 2.31 g (40%>) of 5,6-dichloro-2-(4- oxopentyloxy Nicotinamide as a yellow solid.

According to the analysis of related databases, 142266-62-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC; JARNAGIN, Kurt; AKAMA, Tsutomu; WO2011/94450; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66572-56-3, 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. 66572-56-3, name is 2-Bromoisonicotinic acid, molecular formula is C6H4BrNO2, 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.

Example 21; Synthesis of 2-Bromo-4- . pyridine; [0120] 2-Bromoisonicotinic acid (2.02 g, 0. 010 moles), such as that prepared in Example 23, was dissolved in methylene chloride (20 ml) carbonyldiimidazole (1.8 g, 0.011 moles) was added and the reaction mixture stirred at room temperature for two hours. N, O-Dimethylhydroxylamine hydrochloride (1. 5 g, 0.015 moles) was added in one portion. After stirring overnight the reaction was quenched with 0. 1N NaOH (10 ml), added water and dichloromethane. Separated the layers and extracted the aqueous with dichloromethane (50 ml). The combined organic portion was washed with brine, dried over magnesium sulfate, filtered and stripped to give 2.4 g (98 % yield) of 2-bromo-4- (N- methyl-N-methoxycarboxamide) pyridine. 1H NMR (CDCl3) 3.42 (3H, s), 3.58 (3H, s), 7.15 (1H, d), 7.77 (1H, s), 8.57 (1H, d).

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 66572-56-3, 2-Bromoisonicotinic acid.

Reference:
Patent; DOV PHARMACEUTICAL, INC.; WO2005/84439; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 15862-37-0, 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 15862-37-0, name is 2,5-Dibromo-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,5-dibromo-3-nitropyridine (7.04 g, 25.0 mmol) in 1,4-dioxane (100 mL) and water (25 mL) was added (4-chloro-5-(methoxycarbonyl)thiophen-2-yl)boronic acid (4.51 g, 20.5 mmol), Pd(dppf)C12 (1.34 g,1.64 mmol), and K3P04 (8.73 g, 41.1 mmol) under a N2 stream. The reaction mixture was purged with N2 for 2 mm, heated to 60 C and stirred for 2 h. Then the reaction mixture was cooled to r.t. and extracted with EtOAc (200 mL). The resulting organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using 0-7% EtOAc in hexane to afford the title compound (3.36 g, 43% yield) as a light yellow solid. LC-MS [M+Hj = 376.

According to the analysis of related databases, 15862-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JACOBIO-BETA PHARMACEUTICALS CO., LTD.; JACOBIO-ALPHA PHARMACEUTICALS CO., LTD.; JACOBIO PHARMACEUTICALS CO., LTD.; FANG, Haiquan; ZHOU, Wenlai; HU, Shaojing; CHEN, Mingming; YANG, Guiqun; WANG, Yanping; DU, Yuelei; LI, Qinglong; WU, Tong; WU, Lingjun; LI, Haijun; LONG, Wei; (179 pag.)WO2019/80941; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885267-36-7, 6-Bromo-3-fluoropyridine-2-carbaldehyde, 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 6-Bromo-3-fluoropyridine-2-carbaldehyde, blongs to pyridine-derivatives compound. Quality Control of 6-Bromo-3-fluoropyridine-2-carbaldehyde

Example 73A (2R)-2-{[(6-bromo-3-fluoropyridin-2-yl)methyl]amino}-3-methylbutan-1-ol 6-bromo-3-fluoropicolinaldehyde (4.0 g, 19.61 mmol) and (R)-2-amino-3-methylbutan-1-ol (2.281 mL, 20.59 mmol) were dissolved in methanol (100 mL) and stirred at ambient temperature for 1 hour and 15 minutes. Sodium borohydride (0.742 g, 19.61 mmol) was added and the mixture was stirred for another 1 hour and 30 minutes. The volume of the reaction mixture was reduced, and the mixture was quenched with 200 mL 1.0 N NaOH, and extracted with 200 mL dichloromethane (2*). The organic phase was extracted with 1.0 N HCl and partitioned. The aqueous phase was separated, neutralized with 3.0 N NaOH, extracted with EtOAc, organic phase separated and washed with brine. The organic phase was dried over Na2SO4, filtered, and concentrated to obtain the title compound as an orange solid. MS (ESI+) m/z 291.0 (M+H); 1H NMR (300 MHz, DMSO-d6) delta 7.69 (t, J=8.8, 1H), 7.60 (dd, J=8.6, 3.7, 1H), 4.42 (t, J=5.2, 1H), 3.92-3.75 (m, 2H), 3.43 (dt, J=10.7, 4.8, 1H), 2.34-2.24 (m, 1H), 2.08 (s, 1H), 1.87-1.71 (m, 1H), 0.83 (dd, J=8.5, 6.9, 6H).

The synthetic route of 885267-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; US2012/245124; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 80194-70-3, Adding some certain compound to certain chemical reactions, such as: 80194-70-3, name is 3-Chloro-5-(trifluoromethyl)picolinonitrile,molecular formula is C7H2ClF3N2, 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 80194-70-3.

Description 116; 3-Fluoro-5-trifluoroniethvvridine-2-carbonitrile; A suspension of cesium fluoride (9.6 g, 63 mmol) and potassium carbonate (250 mg, 1.8 mmol) in anhydrous DMSO (50 ml) under N2 was heated to 80C and Description 115 (8.7 g, 42 mmol) was added over 10 min. The reaction mixture was then heated to 95C for 20 min, cooled to 55C and poured into ice water. The mixture was extracted twice with hexane and once with DCM. The combined organic extracts were evaporated to give a solid (8 g, 100%). 1H NMR (400 MHz, CDCl3) 7.91 (1 H, d, J7.6), 8. 84 (1 H, s).

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. 80194-70-3, 3-Chloro-5-(trifluoromethyl)picolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2005/47279; (2005); 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. 1136-52-3, name is (2,2,8-Trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol, molecular formula is C11H15NO3, 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. Computed Properties of C11H15NO3

General procedure: A mixture of alpha4,3-O-isopropylidene pyridoxine, the respective saccharideand molecular sieves (4 A) was stirred under argon atmospherein dry solvent (5 mL) at rt for 1 h before it was cooled to the respectivetemperature T. The promoter was added and the reaction mixture allowedto reach rt overnight. The mixture was diluted with dichloromethane(10 mL) and filtered through a pad of celite. Afterwards,the filtrate was washed with Na2S2O3 (10% in water, 30 mL) and theaqueous phase was extracted with dichloromethane (3 × 40 mL). Thecombined organic layers were washed with distilled water (1×50 mL),brine (1 × 50 mL) and dried over Na2SO4. The solvent was evaporatedunder reduced pressure and the crude product subjected to columnchromatography using SiO2 (pentane/ethyl acetate 1/1 to 1/4, gradientelution) followed by C18 (methanol, isocratic) to afford the glucoside.

With the rapid development of chemical substances, we look forward to future research findings about 1136-52-3.

Reference:
Article; Bachmann, Thomas; Rychlik, Michael; Carbohydrate Research; vol. 489; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem