Tag: M.W:200-300

Application of 56055-54-0, 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. 56055-54-0, name is Methyl 5,6-dichloronicotinate. A new synthetic method of this compound is introduced below.

Step B: Methyl 5-chloro-6- (2, 2, 2-trifluoro-1-methylethoxy) nicotinate; To a solution of 630 mg (3.06 mmol) of methyl 5,6-dichloronicotinate (from Step A) and 349 muL (3.06 mmol) of 1, 1, l-trifluoro-2-propanol in 10 mL of THF at-78 C was added 3.1 mL (3.06 mmol) of sodium bis (trimethylsilyl) amide (1.0 M in THF). After stirring at-78 C for 30 min and at 0 C for 5 h, the reaction was quenched by adding 10 mL of saturated NH4Cl. The mixture was poured into brine and extracted with CH2C12 (3 x 20 mL). Organic layers were combined, dried over MgS04, and concentrated. Chromatography on a Biotage 40M cartridge using 3: 97 v/v Et20/hexanes as the eluant gave 627 mg of the title compound : 1H NMR (500 MHz, CDC13) 8 1.56 (d, J = 6.4, 3H), 3.93 (s, 3H), 5.86 (m, 1H), 8.27 (d, J = 2.1, 1H), 8. 67 (d, J = 2.0, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56055-54-0, Methyl 5,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2005/58848; (2005); 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.832735-56-5, name is 4-Bromo-2-(difluoromethoxy)pyridine, molecular formula is C6H4BrF2NO, molecular weight is 224.0029, as common compound, the synthetic route is as follows.category: pyridine-derivatives

A mixture of C41 (120 mg, 0.467 mmol), C49 (105 mg, 0.469 mmol), tn’s(dibenzylideneacetone)dipalladium(0) (12.8 mg, 14.0 pmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 17.8 mg, 30.8 pmol), and cesium carbonate (608 mg, 1 .87 mmol) in 1 ,4-dioxane (5 mL) was stirred at 100 C for 16 hours. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified using silica gel chromatography (Eluent: 20: 1 petroleum ether / ethyl acetate) to provide the product as a yellow oil. Yield: 50 mg, 0.17 mmol, 36%. 1 H NMR (400 MHz, CDCI3) delta 7.81 (d, J=5.9 Hz, 1 H), 7.42 (t, JHF=73.7 HZ, 1 H), 6.08 (dd, J=5.8, 2.1 Hz, 1 H), 5.75 (d, J=2.0 Hz, 1 H), 4.20-4.1 1 (m, 4H), 3.66 (dd, J=8.0, 5.5 Hz, 2H), 3.20-3.09 (m, 1 H), 2.71 (d, J=7.9 Hz, 2H), 1 .28 (t, J=7.1 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,832735-56-5, 4-Bromo-2-(difluoromethoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; ZHANG, Lei; BUTLER, Christopher Ryan; BECK, Elizabeth Mary; BRODNEY, Michael Aaron; BROWN, Matthew Frank; MCALLISTER, Laura Ann; LACHAPELLE, Erik Alphie; GILBERT, Adam Matthew; (170 pag.)WO2018/2760; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1136-52-3, 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. 1136-52-3, name is (2,2,8-Trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol. A new synthetic method of this compound is introduced below.

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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1136-52-3, its application will become more common.

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

Synthetic Route of 137640-84-7, 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 137640-84-7, name is 6-(3-(Trifluoromethyl)phenoxy)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a 500 mL three-necked flask was added 2-(3-trifluoromethylphenoxy)-6-pyridinecarboxylic acid 28.3 g (0.1 mol),Bis(trichloromethyl) carbonate 11.9 g (0.04 mol) and150 mL of ethyl acetate, magnetically stirred and heated to 35 C.0.3 g of triethylamine was added dropwise, and the reaction was kept at 50 C for 2 h after the addition.Until the bubble stops, the reaction solution is clarified by white turbidity.Then purge the residual hydrogen chloride and phosgene with nitrogen.Standby after cooling.

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 137640-84-7, 6-(3-(Trifluoromethyl)phenoxy)picolinic acid.

Reference:
Patent; Hebei University; Li Wan; Yang Zihui; Yang Fenglin; (6 pag.)CN108794390; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 626-05-1, 2,6-Dibromopyridine, 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, Recommanded Product: 626-05-1, blongs to pyridine-derivatives compound. Recommanded Product: 626-05-1

n-Butyl magnesium chloride (2.0 M in THF, 2.25 ml, 45 mmol) was added to a stirred solution of w-butyl lithium (1.6 M in hexanes, 5.56 ml, 8.9 mmol) at 0C under argon. After 10 minutes at 0C the mixture was cooled to -10C. A solution of 2,6-dibromopyridine (3.0 g, 12.7 mmol) in toluene (35 ml) was added over 10 minutes and the mixture was stirred at -10 for 2 hours. After cooling to -40C, sulfur dioxide gas was bubbled into the mixture for 5 minutes and the reaction was stirred at -40C for 30 minutes. Sulfuryl chloride (1.1 ml, 13.6 mmol) was added and the mixture was allowed to warm to room temperature. The resulting mixture was added over 5 minutes to a stirred mixture of phenol (1.25 g, 13.3 mmol) and triethylamine (7.0 ml, 50.6 mmol) in acetonitrile (30 ml) at 0C. The mixture was stirred at 0C for 30 minutes and then at room temperature for 2 hours. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and dilute sodium bicarbonate solution. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the title product (D7). MS(ES+) m/e 314/316 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,626-05-1, 2,6-Dibromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/10629; (2006); 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.1052714-46-1, name is 6-Bromo-5-fluoropicolinic acid, molecular formula is C6H3BrFNO2, molecular weight is 219.9959, as common compound, the synthetic route is as follows.Recommanded Product: 1052714-46-1

[0273] 6-Bromo-5-fluoro-pyridine-2-carboxylic acid (24.0 g, 109 mmol) was dissolved in a mixture of EtOH (400mL) and cone. H2SO4 (17.5 mL, 328 mmol). The mixture was heated at 90 C for 2.5 h. After cooling to 0 C, a solution of 3.50 M NaOH (90.0 mL, 315 mmol) was slowly added with vigorous stirring (pH adjusted to approx. 4), followed by a sat. solution of NaHC03 until pH was approx. 8. The slurry was filtered through a pad of Celite, and the filtrate was concentrated under reduced pressure. The residue was suspended in cold water (300 mL) and stirred at 0 C for 5 m. The mixture was filtered, washing with water, and the solid was dried under vacuum to provide the title compound as a solid (20.4 g, 75%). XH NMR (500 MHz, (0777) CDC13) delta 8.12 (dd, J = 8.3, 3.6 Hz, 1H), 7.53 (dd, J = 8.3, 7.0 Hz, 1H), 4.47 (q, J = 7.1 Hz, 2H), 1.43 (t, J = 7.1 Hz, 3H). LC-MS (Method C): m/z (ES+), [M+H]+ = 247.8. HPLC tR = 1.74 m.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1052714-46-1, 6-Bromo-5-fluoropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; CUMMING, John, Graham; WU, Frank, Xinhe; EDMAN, Karl, Henrik; CHEN, Hongming; BROWN, Dean, Gordon; BURLI, Roland, Werner; JOHNSTONE, Shawn, Donald; BROWN, Giles, Albert; TEHAN, Benjamin, Gerald; TEOBALD, Barry, John; CONGREVE, Miles, Stuart; (187 pag.)WO2017/194716; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 199522-66-2, 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. 199522-66-2, name is N1-(5-Bromopyrid-2-yl)ethane-1,2-diamine, molecular formula is C7H10BrN3, 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: 3-[2-(5-Bromo-pyridin-2-ylamino)-ethyl]-3H-quinazolin-4-one (compound 75) A suspension of primary amine 73 (1.17 g, 5.40 mmol) and isatoic anhydride 74 (880 mg, 5.40 mmol) in methanol (25 mL) was stirred for 3 h at 50 C. and then concentrated. The resulting oily residue was dissolved in 88% formic acid (20 mL) and refluxed overnight. After removal of formic acid, the solid residue was purified through column chromatography on silica gel (5% methanol in dichloromethane) to give 1.24 g (3.6 mmol, 67% yield) of 75. 13C NMR (300 MHz, CDCl3): 161.6, 156.8, 147.7, 147.6, 147.2, 139.8, 134.5, 127.4, 126.8, 126.3, 121.6, 110.1, 107.0, 46.3, 40.1. LRMS=347.1 (M+1).

According to the analysis of related databases, 199522-66-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MethylGene, Inc.; US2005/288282; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52605-98-8, 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. 52605-98-8, name is 5-Bromo-2,3-dimethoxypyridine, molecular formula is C7H8BrNO2, 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.

As shown in step 2-v of Scheme 2, compound 1005 was suspended in 200 mL of dry THF along with PdCl2(Ph3P)2 (1.56 g, 2.23 mmol) and Ph3P (300 mg, 1.114 mmol). The mixture was flushed with N2 for 10 minutes. Triethylamine (14.0 mL, 10.14 g, 0.1 mol) and trimethylsilylacetylene (11.3 mL, 7.84 g, 0.080 mmol) were added under a nitrogen atmosphere and stirring continued for 15 minutes more before the addition of Cu(I) iodide (500 mg; 2.65 mmol). The reaction mixture was stirred at ambient temperature for 4 hours, and then heated for 5 hours at 40 C. under N2. The mixture was suction filtered through a pad of diatomaceous earth, which was washed with additional THF. The volatiles were removed under reduced pressure. The residue was dissolved in DCM, washed with water (2*), brine, and dried over Na2SO4. After filtration, the volatiles were removed under reduced pressure and the residue purified by silica gel chromatography (DCM) to provide 2,3-dimethoxy-5-((trimethylsilyl)ethynyl)pyridine (5.7 g) as a beige solid: ESMS (M+1)=236; 1H NMR (CDCl3) delta 7.89 (d, J=1.88 Hz, 1H), 7.1 (d, J=1.88 Hz, 1H), 4.02 (s, 3H), 3.89 (s, 3H), 0.12 (s, 9H).

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 52605-98-8, 5-Bromo-2,3-dimethoxypyridine.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; US2011/81316; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64119-42-2, 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. 64119-42-2, name is Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate. A new synthetic method of this compound is introduced below.

(c) Ethyl 6-[4-(5-benzyI-4eta-l,2,4-triazol-3-yl)piperidin-l-yl]-5-cyano-2- methylnicotinateEthyl 6-chloro-5-cyano-2-methyhiicotinate (225 mg, 1.0 mmol)) and the crude 4-(5- benzyl-4H-l,2,4-triazol-3-yl)piperidine (267 mg, 1.1 mmol) were dissolved in EtOH (10 ml) and DIPEA (1 ml) was added. The reaction mixture was heated to 120 0C for 5 min.LCMS showed product and the 1,3, 4- oxadiazole byproduct. NaHCO3 (aq) was added and the mixture was extracted with dichloromethane (x3). The combined organic layer was run through a phase separator and evaporated. The crude product was purified by prepHPLC [Kromasil C8, Gradient: 30 to 60 % (CH3CN/0.1M NH4AcO(aq), pH = 7)] giving ethyl 6-[4-(5-benzyl-4H-l,2,4-triazoltau3-yl)piperidin-l-yl]-5-cyano-2-methyhiicotinate. Yield:38mg (9 % over 3 steps). The 1,3, 4- oxadiazole was not isolated.1HNMR (500MHz, DMSOd6): 1.32 (3H, t, J=7.1Hz), 1.72-1.81 (2H, m), 2.03-2.08 (2H, m), 2.66 (3H, s), 3.05-3.15 (IH, m), 3.29-3.32 (2H, m), 3.99 (2H, s), 4.27 (2H, q, J=7.1), 4.55-4.61 (2H, m), 7.20-7.24 (IH, m), 7.26-7.33 (4H, m), 8.35 (IH, s), 13.45 (IH, br s).MS m/z: 431 (M+l), 429 (M-I).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64119-42-2, Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2008/4942; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 115309-58-5, Adding some certain compound to certain chemical reactions, such as: 115309-58-5, name is N-(tert-Butyl)-6-chloronicotinamide,molecular formula is C10H13ClN2O, 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 115309-58-5.

The intermediate A-1 (1.0 g, 4.7 mmol) was dissolved in 15 ml of tetrahydrofuran and the reaction mixture was cooled to 0 C. O-methylphenylmagnesium chloride (1M in tetrahydrofuran solution, 14.1 mL, 14.1 mmol) was slowly added, and the reaction was kept for 3 hours, then heated to 30 C for 18 h, and then cooled to 0 C. Glacial acetic acid (24 mmol) was slowly added dropwise, and then DDQ (dichlorodicyanobenzoquinone or manganese acetate) (1.6 g, 7.1 mmol) was added to react at room temperature for 1 h.The reaction solution was poured into a 2M sodium carbonate solution, extracted with ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate.After concentration under reduced pressure, it was purified by silica gel column chromatography.Ethyl acetate/petroleum ether (1:1) was used as the mobile phase to give intermediate A-2.The yield of pale yellow solid was 88%.

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. 115309-58-5, N-(tert-Butyl)-6-chloronicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beijing Kuanhou Pharmaceutical Technology Co., Ltd.; Cui Yimin; He Long; Ouyang Liang; Gou Maling; Wang Ling; (39 pag.)CN109384712; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem