Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 90145-48-5, 5-Bromopyridine-2-carboxamide, 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, Computed Properties of C6H5BrN2O, blongs to pyridine-derivatives compound. Computed Properties of C6H5BrN2O

EXAMPLE 251 : 5-(6-(trifluoromethyl)- lH-indazol-4-yl)picolinamide [0794] A vial was charged with a mixture of 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)-6-(trifluoromethyl)-lH-indazole (0.05 g, 0.160 mmol), 5-bromopicolinamide (0.042 g, 0.208 mmol) and PdCl2(dppf) (5.86 mg, 8.01 muiotaetaomicron) in dioxane (8 mL) and aqueous saturated NaHC03 (2 mL). The resulting light brown suspension was heated at 140C for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with a gradient of 25-45% ACN (containing 0.035% TFA) in H20 (containing 0.05% TFA) over a period of 6 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as an off white solid (19 mg, 0.062 mmol, 39%). 1H NMR (400 MHz, DMSO-<) delta ppm 7.66 (s, 1 H), 7.77 (br s, 1 H), 8.06 (s, 1 H), 8.14-8.33 (m, 1 H), 8.37-8.49 (m, 1 H), 9.00-9.08 (m, 1 H), 13.84 (br s, 1 H); ESI-MS m/z [M+H]+ calc'd for Ci4H9F3N40, 307.1; found 307.15. The synthetic route of 90145-48-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; ERICKSON, Philip; FENG, Jun; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; MIURA, Joanne; MURPHY, Sean; TANG, Mingnam; TON-NU, Huong-Thu; WO2013/130855; (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. 186413-75-2, name is 3-Bromo-6-chloro-2-methyl-5-nitropyridine, molecular formula is C6H4BrClN2O2, 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. SDS of cas: 186413-75-2

To a stirred solution of 3-bromo-6-chloro-2-methyl-5-nitropyridine (2.00 g, 7.95 mmol) in tetrahydrofuran (16 mL) at -78 C. was added (E)-but-2-en-2-ylmagnesium bromide (0.5M in THF) (55.7 mL, 27.8 mmol). The reaction mixture was allowed to warm to ?35 C. over 30 min. and was then quenched with a saturated aqueous solution of ammonium chloride. The mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of ammonium chloride, washed with brine, and dried over anhydrous sodium sulfate. The organic layer was collected, and the aqueous layers were sequentially washed extracted with ethyl acetate (2*). The combined organic layers were dried over anhydrous sodium sulfate, and the resulting residue was purified by ISCO flash silica gel chromatography (24 g column; gradient: 0%-100 ethyl acetate in hexane) to give 4-bromo-7-chloro-2,3,5-trimethyl-1H-pyaolo[2,3-c]pyridine (0.402 g, 1.47 mmol, 19% yield) as a yellow solid. The product had a UPLC ret. time=1.14 min. -Column: PHENOMENEX Kinetex C18 2.1×50 mm (1.5 min. gradient); Solvent A=10% MeCN, 90% H2O, 0.1% TFA; Solvent B=90% MeCN, 10% H2O, 0.1% TFA. LC/MS M+1=273.2 and 275.2.

With the rapid development of chemical substances, we look forward to future research findings about 186413-75-2.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Liu, Qingjie; Watterson, Scott Hunter; Batt, Douglas G.; Ahmad, Saleem; Beaudoin Bertrand, Myra; Gong, Hua; Guo, Weiwei; Macor, John E.; Ngu, Khehyong; Tebben, Andrew J.; Tino, Joseph A.; (177 pag.)US2016/115126; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17570-98-8 , The common heterocyclic compound, 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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.

N-({[(fra/?s-4-{[(methylethyl)sulfonyl]amino}cyclohexyl)methyl]amino}thioxomethyl) amide (0.60 g, 2.0 mmol) was added to a stirred solution of 2-bromo-1-(2- pyridyl)ethan-1-one hydrobromide (0.57 g, 2.0 mmol) in EtOH (20 ml_) at rt followed by the addition of DIEA (1.05 ml_, 6.0 mmol). The reaction mixture was heated at reflux for 4 h, cooled to rt, and concentrated in vacuo. The resultant residue was re- dissolved in CHCI3 and washed successively with aqueous citric acid, water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (60 % EtOAc in Hexanes) to afford the desired product as a tan colored solid (0.56 g, 69 %). 1H NMR (CDCI3) delta 8.58 (d, 1 H, J=4.8 Hz), 7.89 (dt, 1 H, J=7.6 and 1.2 Hz), 7.71 (td, 1 H, J=7.8 and 2.0 Hz), 7.17 (td. 1 H, J=4.8 and 1.2Hz), 5.25 (br s, 1 H), 3.85 (d, 1 H1 J=8.4 Hz), 3.25 (br m, 1 H), 3.18 (t, 2H, J=6.4 Hz), 2.14 (dt, 2H, J=12.0 and 1.2 Hz), 2.19 (br, d, EPO 2H, J=12.8 Hz), 1.62 (br m, 3H), 1.38 (d, 6H, J=6.8 Hz), 1.25 (dq, 2H, J=12.8 and 1.6 Hz). LC-MS m/e: 395 (M+H)+; tR = 2.14 min (Method-A).

The synthetic route of 17570-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2007/2126; (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. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 6-Chloro-5-nitronicotinic acid

a. To a solution of 6-chloro-5-nitronicotinic acid in acetic acid (240 ml) was added iron (20 g) and the mixture was heated with stirring on a steam bath. After 11/2 hours, the mixture was filtered hot and washed with hot acetic acid. The filtrate was concentrated to dryness and the residue was treated with 10% NaOH, filtered and the pH adjusted to 2-3. The solid was filtered to yield 8.0 g (60% yield) of 5-amino-6-chloronicotinic acid.

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US4279913; (1981); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1206978-11-1 ,Some common heterocyclic compound, 1206978-11-1, molecular formula is C6H3BrF3NO, 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.

3-Trifluoromethoxy picolinic acid (24); At -100 0C, butyllithium (1.56 M in hexane, 5.5 mL, 8.3 mmol, 1 eq) was added dropwise to a solution 2-bromo-3-trifluoromethoxy pyridine (23, 2.0 g, 8.3 mmol) in dried toluene (15 mL). After 2 h at -78 0C, the mixture was poured onto an excess of freshly crushed dry ice before being treated with an aqueous solution of sodium hydroxide (5%, 15 mL). The resulting aqueous layer was collected, washed with diethylether (10 mL) and acidified to pH 4 by dropwise addition of hydrochloric acid (6N, 4 mL) before being extracted with ethyl acetate (3 x 10 mL). The combined organic layers were dried over sodium sulfate and evaporated to afford pure 3-trifluoromethoxy picolinic acid (24, 1.1 g, 5.3 mmol, 64%) as a white powder; m.p. 84-87 0C.1H NMR (CD3OD, 300 MHz): delta = 8.54 (d, J= 4.5 Hz, 1 H), 7.87 (d, J = 8.5 Hz, 1 H), 7.63 (dd, J= 8.5, 4.5 Hz, 1 H). – 19F NMR ((CD3)2CO, 282 MHz): delta = -58.7 – 13C NMR(CD3OD, 75 MHz): delta = 164.5, 147.5, 144.5, 143.4, 131.2, 127.6, 120.3 (q, J= 260 Hz).- C7H4F3NO3 (207): calcd. (%) C 40.59, H 1.95, N 6.76; found C 40.21, H 2.17, N 6.97.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206978-11-1, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866546-09-0, Adding some certain compound to certain chemical reactions, such as: 866546-09-0, name is 3-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine,molecular formula is C7H4BrClN2, 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 866546-09-0.

[0231] Step 2: l-(Benzenesulfonyl)-3-bromo-5-chloro-pyrrolo[2,3-b]pyridine. NaH (60% dispersion in oil, 0.33 g, 8.3 mmol) was added to a solution of 3-bromo-5-chloro-lH- pyrrolo[2,3-b]pyridine (1.28 g, 5.5 mmol) in DMF (25 mL) at room temperature. The reaction was stirred for 10 min. and then /?-toluenesulfonyl chloride (1.06 mL, 8.3 mmol) was added and the reaction stirred for an additional 2 h. Water (50 mL) was added, the mixture extracted with EtOAc (3 x 50 mL), the organic layers combined, dried over sodium sulfate, filtered and evaporated to dryness. Purification by column chromatography (hex/EtOAc) and recrystallization from hex/EtOAc afforded the desired product (1.45 g, 70%). 1H NMR (400 MHz, DMSO- e) delta ppm 8.50 (d, 1 H), 8.35 (s, 1 H), 8.13 (dd, 1H), 8.12 (d, 2H), 7.76 (dt, 1 H), 7.65 (t, 2 H).

According to the analysis of related databases, 866546-09-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALZHEIMER’S INSTITUTE OF AMERICA, INC.; SEBAHAR, Paul R.; HALTER, Robert J.; MCLEOD, Donald A.; PARKER, Daniel P.; YAGER, Kraig M.; SHENDEROVICH, Mark D.; HOLCOMB, Ryan C.; RICHARDS, Burt; BARTEL, Paul L.; KIM, Se-Ho; SLATTUM, Paul M.; TANGALLAPALLY, Rajendra; TROVATO, Richard; YUNGAI, Ashantai J.; WO2014/4863; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 880870-13-3, 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

Step B: 6-Chloro-4-methoxypyridine-3-carbonitrile: A solution of 5-bromo-2-chloro-4- methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, 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 95 C for 12 h under nitrogen. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,880870-13-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alex; SUZUKI, Takao; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda K.; WO2015/96035; (2015); 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 885168-04-7, name is 5-Bromo-3-chloropicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 885168-04-7

2) In tetrahydrofuran (27 mL) was dissolved 5-bromo-3-chloro-N-methoxy-N-methyl- pyridine-2-carboxamide (2.66 g), the mixture was cooled under nitrogen atmosphere at -70C or lower, and a tetrahydrofuran (5 mL) suspension of lithium aluminum hydride (180 mg) was added dropwise to the mixture. The mixture was stirred at -70C or lower for 2 hours, then, water (10 mL) and a saturated brine (10 mL) were added dropwise to the mixture. A temperature of the mixture was raised to room temperature, the mixture was extracted with ethyl acetate, and the organic layer was washed with water and a saturated brine. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=100:0 to 90: 10) to obtain a mixture of an aldehyde compound and an aldehyde equivalent (2.1 g). To water (36 mL) were added 3,3-dibromo-l,l,l-trifluoropropan-2-one (6.61 g) and sodium acetate (4.02 g) and the mixture was stirred at 95C for 30 minutes. An aqueous solution obtained by ice-cooling the mixture was added to a mixture comprising the previously obtained mixture of the aldehyde/ aldehyde equivalent (1.8 g), 28% aqueous ammonia (18 mL) and methanol (36 mL) at room temperature, and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated, the residue was extracted with ethyl acetate, and the organic layer was washed with a saturated brine, and then, dried over anhydrous magnesium sulfate. After concentrating the mixture under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=80:20), and the obtained solid was collected by filtration, washed with isopropyl ether and dried to obtain 5-bromo-3-chloro-2-[5- (trifluoromethyl)-lH-imidazol-2-yl]pyridine (935 mg).MS (m/z): 326/328/330 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 885168-04-7.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; SAKURAI, Osamu; SARUTA, Kunio; HAYASHI, Norimitsu; GOI, Takashi; MOROKUMA, Kenji; TSUJISHIMA, Hidekazu; SAWAMOTO, Hiroaki; SHITAMA, Hiroaki; IMASHIRO, Ritsuo; WO2012/81736; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 669066-89-1, 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. 669066-89-1, name is 3-Amino-5-bromopicolinamide. A new synthetic method of this compound is introduced below.

(b) 3-Amino-5-bromopicolinic acid. A mixture of 3-amino-5- bromopicolinamide (28.2 g, 0.13 mol) and concentrated HCl (361 inL) was heated at reflux for 12 hours. The reaction mixture was allowed to reach room temperature, and the solid which precipitated was filtered. The filter cake was dissolved in water, and the pH of the aqueous solution was adjusted to pH = 4 with saturated NaOAc, and extracted with EtOAc (3 x). The combined organic extracts were dried over anhydrous MgSO4, and filtered. The filtrate was evaporated under reduced pressure, and the residue dried in vacuo to afford the title compound as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,669066-89-1, 3-Amino-5-bromopicolinamide, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2008/76425; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1186637-43-3 ,Some common heterocyclic compound, 1186637-43-3, molecular formula is C7H5BrN2O, 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 2-(tert-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and 3-bromo-6-methoxypicolinonitrile (from step 1) (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(triphenyl-phosphine)palladium (5 mol %) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 100 C. and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-50% ethyl acetate in hexane to give 3-methoxybenzo[f][1,7]naphthyridin-5-amine as a yellow solid. 1H NMR (acetone d-6): delta 8.91 (d, 1H), 8.34 (d, 1H), 7.63 (d, 1H), 7.51-7.53 (dd, 1H), 7.27-7.33 (m, 2H), 6.65 (br, 2H), 4.11 (s, 3H). LRMS [M+H]=226.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1186637-43-3, its application will become more common.

Reference:
Patent; GlaxoSmithKline Biologicals SA; Skibinski, David; Jain, Siddhartha; Singh, Manmohan; O’Hagan, Derek; (124 pag.)US9408907; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem