Pyridine-derivatives

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 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 956010-87-0

To compound 12 (150 mg, 0.80 mmol) and N-methyl-N-phenylhydrazinecarbothioamide (174 mg, 0.96 mmol) was added a 1N aqueous sodium hydroxide solution (3.0 mL), and the mixture was heated in a microwave oven to 150 C for 10 min. The mixture was diluted with water and extracted twice with ethyl acetate. The solvent was evaporated, and the residue was purified by preparative HPLC to yield 159 mg (64 %) of the title compound as a tan solid. 1H NMR (400 MHz, DMSO-d6): delta 3.60 (s, 3H), 7.35-7.40 (m, 2H), 7.52 (t, J=7.7Hz, 2H), 7.56-7.59 (m, 2H), 8.60 (dd, J=7.3, 1.5Hz, 1H), 8.64 (dd, J=4.4, 1.5Hz, 1H), 14.13 (s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 40.61, 111.6, 118.5, 124.5, 127.0, 130.0, 130.8, 136.0, 146.5, 150.1, 151.7, 152.5, 169.3. HRMS m/z calcd for C15H12N6S + [H+]: 309.0917; found: 309.0908.

With the rapid development of chemical substances, we look forward to future research findings about 956010-87-0.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58553-48-3, 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. 58553-48-3, name is 5-(Hydroxymethyl)picolinonitrile, molecular formula is C7H6N2O, 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 46A (6-Cyanopyridin-3-yl)methyl methanesulfonate 3.51 ml (27.14 mmol) of N,N-diisopropylethylamine and 2.87 ml (25.05 mmol) of methanesulfonic acid chloride were added successively to a solution of 2.8 g (20.87 mmol) of 5-(hydroxymethyl)pyridine-2-carbonitrile [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 50 ml of anhydrous methylene chloride at 0 C. The reaction mixture was then stirred at RT for 1 h. 10 ml of water were then added, the phases were separated and the aqueous phase was extracted twice with approx. 10 ml of methylene chloride each time. The combined organic extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and freed from the solvent on a rotary evaporator. The residue obtained was separated into its components by means of MPLC (silica gel, cyclohexane/ethyl acetate 1:1). 2.12 g (48% of th.) of the title compound (for the analytical data see below) and 1.51 g (47% of th.) of the compound described in Example 45A were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 8.76 (d, 1H), 7.93 (dd, 1H), 7.78 (d, 1H), 5.32 (s, 2H), 3.10 (s, 3H). MS (DCI, NH3): m/z=213 [M+H]+, 230 [M+NH4]+. LC/MS (method F, ESIpos): Rt=0.57 min, m/z=213 [M+H]+.

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 58553-48-3, 5-(Hydroxymethyl)picolinonitrile.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; Haerter, Michael; Beck, Hartmut; Ellinghaus, Peter; Berhoerster, Kerstin; Greschat, Susanne; Thierauch, Karl-Heinz; Suessmeier, Frank; US2013/196964; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 868551-30-8, 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. 868551-30-8, name is Methyl 4-methyl-5-nitropicolinate, molecular formula is C8H8N2O4, 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.

To a stirring solution of methyl 4- methyl-5-nitro-pyridine-2-carboxylate (3.00 g) in THF (40 mL) was added Pd/C catalyst (300 mg). The flask was evacuated and back-filled with hydrogen from a balloon three times and then stirred under hydrogen overnight. The mixture was filtered through Celite, and the filter cake was extracted several times with ethyl acetate. The combined organic extracts were concentrated and the resulting white powder (2.58 g, 100%) consisting of methyl 5-amino-4-methyl-pyridine-2-carboxylate was used in the next step without further purification and characterization. To a stirring solution of methyl 5- amino-4-methyl-pyridine-2-carboxylate (2.58 g, 15.53 mmol) in AcOH (60 mL), was added 2.0 M sodium nitrite in water (9.3 mL, 18.63 mmol) and the mixture was stirred for 4 h at room temperature. The acetic acid and other volatiles were removed at high vacuum, the resulting solid was suspended in water and filtered to give the title compound as a yellowish solid (2.18 g, 79% yield). (at)HNMR (DMSO-d6) : 8 ppm 13.98 (bs, 1 H), 9.10 (s, 1 H), 8.57 (s, 1 H), 8.39 (s, 1 H), 3.88 (s, 3H). LCMS (API- ES M+Na+) 200.

According to the analysis of related databases, 868551-30-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2005/103003; (2005); 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

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

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

Related Products of 3279-76-3, 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.3279-76-3, name is 6-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, molecular weight is 109.13, as common compound, the synthetic route is as follows.

1) 3-Bromo-2-methoxy-5,8-dimethyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine A mixture of 2-hydroxy-6-methylpyridine (164 g, 1.47 mol), iodomethane (1.35 kg, 9.53 mol), Ag2CO3 (526 g, 1.91 mol) in THF (10 ml) was strirred overnight at ambient temperature while protecting from light. The mixture was filtered through Celite and the filter cake was washed with THF. The filtrate was concentrated in vacuo until all methyl iodide was removed by HPLC analysis to yield 145.6 g (80%) of 2-methoxy-6-methylpyridine.

The chemical industry reduces the impact on the environment during synthesis 3279-76-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Forest Laboratories Holdings Limited; US2007/281918; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113118-82-4, 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. 113118-82-4, name is 5-Chloronicotinaldehyde. A new synthetic method of this compound is introduced below.

n-Butyllithium (2.063ml, 5.16 mmol) was added to -40 C solution of 1 -bromo-4-(trifluoromethyl)benzene (0.722 ml, 5.16 mmol) in THF (30 ml) and this solution was stirred at -40 C for 1 h. A solution of 5-chloronicotinaldehyde (730 mg, 5.16 mmol) in THF (5 mL) was added and the solution was stirred at -40 C for 1 h and then at 0 C for 1 h. The reaction was then quenched with saturated aqueous NH4C1 solution. The product was extracted with ethyl acetate. The organic extract was dried over Na2504, filtered, and concentrated. No further purification is necessary. ?H NMR (500 MHz, CDC13) oe: 8.54 (s, 1H), 8.48 (s, 1H), 7.78 (s, 1H), 7.66 (d, J= 8 Hz, 2H), 7.53 (d, J= 8 Hz, 2H), 5.97(s, 1H), 3.55 (broad s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-82-4, 5-Chloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; WILSON, Jonathan, E.; MCCRACKEN, Troy; (95 pag.)WO2016/179059; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53554-20-4, Adding some certain compound to certain chemical reactions, such as: 53554-20-4, name is 6-Amino-2-chloronicotinonitrile,molecular formula is C6H4ClN3, 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 53554-20-4.

To a 40 mL pressure vial were added 6-amino-2-chloronicotinonitrile (1.000 g, (0806) 6.51 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (1.423 g, 8.47 mmol), K2CO3 (1.350 g, 9.77 mmol), followed by 1,2-dimethoxy ethane (16 mL), water (8 mL) and then Pd(PPh3)4 (0.226 g, 0.195 mmol). Argon was bubbled through the mixture. The reaction mixture was heated at 80 C overnight in a heating block. The reaction mixture was cooled to room temperature, diluted with EtOAc, and washed with brine. (0807) The organic layer was separated and concentrated. The material was purified using silica gel chromatography eluting with 0-80% B/DCM over 13 minutes. [B= 10% 2 N NH3 in MeOH/EtOAc]. The appropriate fractions were concentrated to afford 6-amino-2-(prop- l-en-2-yl)nicotinonitrile (0.878 g, 5.52 mmol, 85% yield), as an off-white solid. NMR (400 MHz, DMSO-de) delta 7.70 (d, J=8.8 Hz, IH), 7.01 (br. s., 2H), 6.42 (d, J=8.8 Hz, IH), 5.49-5.43 (m, 2H), 2.07 (t, J=l. l Hz, 3H).

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. 53554-20-4, 6-Amino-2-chloronicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ARAUJO, Erika M. V.; CHEN, Yan; DASGUPTA, Bireshwar; DEGNAN, Andrew P.; HILL, Matthew D.; KUMI, Godwin Kwame; MASTALERZ, Harold A.; WITTMAN, Mark D.; PEARCE, Bradley C.; ZHANG, Guifen; (172 pag.)WO2019/90198; (2019); 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