Tag: M.W:200-300

Reference of 1256561-65-5, 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 1256561-65-5, name is 3-(Bromomethyl)-5-fluoropyridine hydrobromide. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3 -(bromomethyl)-5 -fluoro-pyridine hydrobromide AA (53 mg, 0.19 mmol, 2.1 eq.) and sodium hydride (6.6 mg, 0.28 mmol, 3.0 eq.) in DMF (500 1iL) were stirred for 10 minutes. Compound Z (prepared according to methods described in Example 5) (25 mg, 0.092 mmol, 1.0 eq.) was added. After 18 hours, the reaction was diluted with ethyl acetate and washed with water and brine twice. The organic layerss were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by reverse phase HPLC afforded 12.8 mg (3 7%) of the title compound. ?H NMR (400 MHz, DMSO-d6) (5 8.47 (d, J= 2.8 Hz, 1H), 8.43 (s, 1H), 8.25 (s, 1H), 7.66 (s, 1H), 7.57- 7.53 (m, 2H), 7.36 (dd, J 1.92, 9.72 Hz, 1H), 7.29-7.25 (m, 2H), 4.41 (s, 2H), 3.49 (t, J= 5.2 Hz, 2H), 3.18 (t, J= 5.2 Hz, 2H), 2.76 (s, 3H); ES-MS [M+1]: 381.2.

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 1256561-65-5, 3-(Bromomethyl)-5-fluoropyridine hydrobromide.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, P. Jeffrey; LINDSLEY, Craig, W.; EMMITTE, Kyle A.; FELTS, Andrew S.; BOLLINGER, Katrina A.; (140 pag.)WO2016/149324; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 951625-93-7, 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.951625-93-7, name is Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, molecular formula is C9H7ClN2O2, molecular weight is 210.62, as common compound, the synthetic route is as follows.

[0168] To a solution of methyl 4-chloro-lH-pyrrolo[2,3-b]pyridine-5-carboxylate (2.3 g, 11 mmol) in dimethylformamide (DMF; 20 mL) was added NaH (0.67 g, 17 mmol, 60% purity) under nitrogen. The mixture was stirred at 0 C for 0.5 hours. To this was added chloromethyl methyl ether (1.1 g, 13 mmol, 1 mL) and the reaction was stirred at 25 C for 2 hours. Upon completion, the reaction mixture was quenched by addition aqueous saturated NH4C1 solution (20 mL) and diluted with water (10 mL). The mixture was extracted with ethyl acetate (3x 40 mL). Organic layers were combined, washed with brine (2x 25 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give methyl 4-chloro-l-(methoxymethyl)-lH-pyrrolo[2,3-b]pyridine-5- carboxylate (2.3 g, 8.6 mmol, 78% yield) as a yellow solid.

Statistics shows that 951625-93-7 is playing an increasingly important role. we look forward to future research findings about Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate.

Reference:
Patent; SYROS PHARMACEUTICALS, INC.; ZHANG, Yi; AUSTGEN, Kathryn; CHUAQUI, Claudio Edmundo; MALOJCIC, Goran; SINKO, William; GUAN, Huiping Amy; SAVOIE, Tracey Lodie; (92 pag.)WO2018/191587; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 443956-08-9, 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. 443956-08-9, name is 6-Bromo-2-nitropyridin-3-ol. A new synthetic method of this compound is introduced below.

To a stirred solution of 6-bromo-2-nitropyridin-3-ol (6 g, 27.40 mmol) in EtOH (100 mL) was added iron (11.00 g, 197.00 mmol), calcium chloride (3.04 g, 27.4 mmol) and the reaction mixture for was heated at 85 C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through celite and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Redisep-80 g, 10-20% MeOH/DCM) to obtain Intermediate 115A (3.00 g, 57.90%) as a yellow solid.1H NMR (400 MHz, DMSO-d6) delta ppm 6.50 (d, J = 7.78 Hz, 1 H), 6.75 (d, J = 7.78 Hz, 1 H), 9.70 (br. s, 1 H). (2 Exchangeable proton not observed). LCMS (Method-O): retention time 0.64 min, [M+2H] 191.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,443956-08-9, 6-Bromo-2-nitropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 185017-72-5, 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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows.

(5-Bromo-6-methoxy-pyridin-2-yl)-methanol (356a) step a-To a solution of 3-bromo-2-chloro-6-methyl-pyridine (2.0 g, 0.687 mmol) in CHCl3 was added MCPBA (3.3 g, 19.1 mmol) and the resulting solution was heated at 50 C. overnight. The resulted solution was cooled and partitioned between DCM and sat’d. aq. NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluding with an EtOAc/hexane gradient (30 to 80% EtOAc) to afford 1.88 g (87%) of 3-bromo-2-chloro-6-methyl-pyridine 1-oxide (357a) as a white solid. step b-A solution of 357a (0.5 g) and 0.5 M NaOMe/MeOH (4.9 mL) was stirred at RT overnight. The reaction mixture was concentrated in vacuo and the residue loaded on a SiO2 column and eluted with 5% MeOH/DCM to afford 3-bromo-2-methoxy-6-methyl-pyridine 1-oxide (357b).

According to the analysis of related databases, 185017-72-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2010/21423; (2010); 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. 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 1083057-12-8

Preparation of 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0.3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45 C. After completion of the phthalic anhydride addition, the mixture was heated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2SO3 (1.5 eq) was added via addition funnel. After completion of Na2SO3 addition, the mixture was stirred for an additional 30 min and the layers separated. The organic layer was stirred and 10% wt/wt aqueous. Na2CO3 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) that was used directly in the next step.

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, 1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Verwijs, Marinus Jacoubus; US2013/186801; (2013); 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. 1201676-03-0, name is 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, molecular formula is C7H4Cl2N2O, 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. Quality Control of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

4,6-Dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (5.63 g, 27.7 mmol), te/f-butyl piperazine-1-carboxylate (7.75 g, 41.6 mmol), triethylamine (14.Og, 139 mmol), and dioxane (50 ml.) are stirred at 120 0C in a 350 ml. sealed tube for 16 h. To the cooled down reaction mixture are then added more te/f-butyl piperazine-1-carboxylate (5.2 g, 27.7 mmol) and triethylamine (2.83 g, 28.0 mmol). The vessel is sealed again and stirred at 120 0C for 24 h. The reaction mixture is then cooled to ambient temperature, and a light-pink solid is isolated by filtration (6.18 g, 17.5 mmol, 63%). MS(ESI) m/z 353.15 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.04 (s, 1 H), 6.89 (s, 1 H), 4.57 (s, 2 H), 3.61 – 3.54 (m, 4 H), 3.47 – 3.41 (m, 4 H), 1.42 (s, 9 H).D. 4-(4-Chloro-1 -oxo-2,3-dihydro-1 H-pyrrolo[3,4-c]pyridin-6-yl)-piperazine-1 -carboxylic acid terf-butyl ester. The title compound is typically obtained from the dioxane filtrate after isolation of 4- (6-chloro-1 -oxo-2,3-dihydro-1 /-/-pyrrolo[3,4-c]pyridin-4-yl)-piperazine-1 -carboxylic acid tert- butyl ester. The dioxane is removed by rotary evaporation. Treatment with methanol yields a light yellow solid which is isolated by filtration. MS(ESI) m/z 353.30 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 8.93 (s, 1 H), 7.01 (s, 1 H), 4.28 (s, 2 H), 3.58 – 3.53 (m, 4 H), 3.45 – 3.40 (m, 4 H), 1.42 (S, 9 H).

With the rapid development of chemical substances, we look forward to future research findings about 1201676-03-0.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3430-18-0, Adding some certain compound to certain chemical reactions, such as: 3430-18-0, name is 2,5-Dibromo-3-methylpyridine,molecular formula is C6H5Br2N, 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 3430-18-0.

[0231] A solutionof2,5-dibromo-3-methylpyridine (1) 3 g,12.1 mmol) in methanol (20 ml) was added sodium methoxide(2M, 20 mL) and refluxed at 100 C. for 2 h. The reactionmixture was poured on ice water and neutralized with aqueoushydrochloric acid (1M) and extracted with dichloromethane(2×15 ml). The combined organic layer waswashed with water, brine, dried over sodium sulfate, andconcentrated at reduced pressure to give 5-Bromo-2-methoxy-3-methyl-pyridine (35), which was used without furtherpurification (1.9 g, 77.8%).

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. 3430-18-0, 2,5-Dibromo-3-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Naik, Maruti N.; PEER MOHAMED, Shahul Hameed; Shandil, Radha K.; Shinde, Vikas Narayan; Shirude, Pravin S.; Chatterji, Monalisa; US2015/25087; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 405224-23-9, 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. 405224-23-9, name is 5-Bromo-2-chloronicotinonitrile. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-2-chloronicotinonitrile (1.0 equiv.) in THF and water (4:1, 0.2M) was added potassium carbonate (3.0 equiv.) and 4-methyl-3-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)aniline (1.0 equiv.) and the solution was degassed with Argon. PdCl2(dppf)-DCM (0.1 equiv.) was added and the solution was refluxed at 90 C for 24 hours. Upon cooling to room temperature, the reaction was partitioned between 1:1 EtOAc/n- heptanes and H2O, mixed, separated, washed with NaCl (sat.) , dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography (0-80% EtOAc/n-heptanes) to yield 5-(5-amino-2-methylphenyl)-2-chloronicotinonitrile in 82% yield. LCMS (m/z) (M+H) = 243.9, Rt = 0.56 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,405224-23-9, its application will become more common.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul Andrew; BURGER, Matthew T.; LOU, Yan; NISHIGUCHI, Gisele A.; POLYAKOV, Valery Rostislavovich; RAMURTHY, Savithri; SUBRAMANIAN, Sharadha; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (180 pag.)WO2016/38583; (2016); 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. 436799-32-5, name is 5-Bromo-2-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C6H3BrF3N

In a dried 250 mL 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (16 mL, Aldrich, inhibitor free) followed by N, N-diisopropylamine (0.895 g, 8.85 mmol, Aldrich, redistilled 99.95% pure). After cooling the stirred solution to -70 0C, n-butyl lithium (3.54 mL of a 2.5M solution in hexanes, 8.85 mmol) was added dropwise, keeping the reaction temperature less than -60 0C. The resulting solution was stirred at -70 0C for a further 10 min, then warmed to -20 0C, before immediately cooling to -90 0C. A solution of 5-bromo-2-(trifluoromethyl)pyridine (2 g, 8.85 mmol) in anhydrous THF (8 ml_, Aldrich, inhibitor free) was added dropwise, keeping the reaction temperature less than -85 0C. The resulting orange solution was stirred at -90 0C for 40 min.In a separate dried 250 ml_ 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (5 ml_, Aldrich, inhibitor free) followed by methyl iodide (5 ml_, 80 mmol). The solution was cooled to -90 0C. To this was added (via cannula) the solution of the pre-formed lithiated pyridine, controlling the rate so as to keep the reaction temperature of the receiving flask less than -80 0C. The resulting dark solution was stirred at -90 0C for a further 15 min (LCMS indicated reaction complete). The reaction was quenched with sat aq. NH4CI solution (50 mL), then allowed to slowly warm to rt. Organics were extracted with EtOAc (2 x 50 mL), then the combined organic layers washed with water (50 mL), then brine (50 mL), separated, dried over MgSO4, and then filtered. Concentration in vacuo gave 1.68 g of a brown oil which was purified via short-path vacuum distillation (45-46 0C, ca. 5 mmHg) to give 5-bromo-4-methyl-2- (trifluoromethyl)pyridine 1-2 (0.289 g, 14%) as a yellow oil (>97% pure). MS (M + H)+: 241.8, tR = 2.458 min (method 1); 1H NMR (CDCI3) delta 8.74 (1H, s), 7.56 (1H, s), 2.50 (3H, s).

The synthetic route of 436799-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124614; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 880870-13-3 , The common heterocyclic compound, 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, molecular formula is C6H5BrClNO, 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 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged nitrogen for 15 min. Next, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95C for 12 h under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0 – 30% ethyl acetate/hexanes to afford the product. 1HNMR (500 MHz, DMSO- 6) delta 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC/MS: [(M+l)]+ = 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.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem