Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 78607-36-0, 2-Chloro-3-iodopyridine, 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 C5H3ClIN, blongs to pyridine-derivatives compound. Computed Properties of C5H3ClIN

To a flame-dried flask were added Pd(PPh3)4 (10 mol %), Xantphos (10 mol %), Cs2CO3 (3 eq) and 2-chloro-3-iodopyridine (1.2 eq). Then, 6SB (1 eq) and DMF (0.15 M) were added to the reaction mixture under an N2 atmosphere. The reaction mixture was stirred for 10 min at room temperature, and then heated at 140 C. in a pre-heated oil bath for 24 h. After that, the reaction mixture was cooled to room temperature, diluted with CH2Cl2, filtered through a short pad of Celite, and washed with CH2Cl2. The combined organic extracts were concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel to provide the product DFE-6SB-2 in 39% yield.

The synthetic route of 78607-36-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arizona Board of Regents on behalf of Arizona State University; Li, Jian; Zhu, Zhi-Qiang; (232 pag.)US2018/337345; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6000-50-6, 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride, 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, Safety of 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride, blongs to pyridine-derivatives compound. Safety of 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride

To a solution of 6-(4-aminophenyl)-4-(quinolin-7-yl)pyridazin-3(2H)-one, (800 mg, 2.54 mmol), in tetrahydrofuran, 160 mL, was added 4-nitrophenyl carbonochloridate (615 mg, 3.05 mmol). The reaction mixture was heated at 60 C for 5 hours and concentrated under vacuum. The residue was dissolved in N,N-dimethylformamide, 20 mL and added to 2,3- dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride (588 mg, 2.54 mmol) and N,N- diisopropylethylamine, (2.21 mL, 12.7 mmol) in dichloromethane (60 mL) and stirred at r.t. for 16 hours. The precipitate was collected by filtration, washed with water and dried to give the desired product, 850 mg (98% purity, 65% yield over two steps).PRODUCTS: (1029) LC-MS (Method 3): Rt = 0.32 min; MS (ESIpos): m/z = 461 [M+H]+ 1H-NMR (400 MHz, DMSO-D6) delta [ppm]: 4.79-4.81 (m, 4H), 7.41 (d, 1H), 7.54-7.57 (m, 1H), 7.68-7.71 (m, 2H), 7.91-7.93 (m, 2H), 8.03-8.05 (m, 1H), 8.15-8.17 (m, 1H), 8.31 (s, 1H), 8.38-8.40 (m, 1H), 8.46-8.48 (m, 1H), 8.58-8.60 (m, 2H), 8.74 (s, 1H), 8.93-8.94 (m, 1H).

The synthetic route of 6000-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BOeHNKE, Niels; BERGER, Markus; SOMMER, Anette; HAMMER, Stefanie; FERNANDEZ-MONTALVAN, Ernesto, Amaury; STELTEN-LUDWIG, Beatrix; GUeNTHER, Judith; MAHLERT, Christoph; GREVEN, Simone; SARKER, Abul, Basher; TAIT, Michael; (451 pag.)WO2019/149637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72587-15-6, 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. 72587-15-6, name is 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine, molecular formula is C6H2ClF3N2O2, 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.

Production Example 43(1) A mixture of 2-chloro-3-nitro-5- trifluoromethylpyridine (2.60 g), 2 , 2 , 2-trifluoroethylamine (0.79 g) , N, N-diisopropylethylamine (1.04 g) and N-methyl- 2-pyrrolidone (5 ml) was stirred at room temperature for 10 hours. To the reaction mixture was poured aqueous 10% citric acid solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give ( 3-nitro-5-trifluoromethylpyridin- 2-yl) – (2, 2, 2-trifluoroethyl) amine (1.83 g) . ( 3-nit o-5-trifluoromethylpyridin-2-yl ) – ( 2 , 2 , 2- trifluoroeth l ) amine 1H-N R (CDCI3) delta: 8.72 (lH,d), 8.68 (lH,d), 8.59 (lH,brs), 4.54- .41 (2H,m) .

According to the analysis of related databases, 72587-15-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; TAKAHASHI, Masaki; TANABE, Takamasa; ITO, Mai; NOKURA, Yoshihiko; IWATA, Atsushi; WO2013/18928; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1005291-43-9, 2-Bromo-5-fluoroisonicotinaldehyde, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

2-Bromo-5-fluoroisonicotinaldehyde (2 g, 9.80 mmol) and hydroxylamine hydrochloride (1.022 g, 14.71 mmol) were dissolved in methanol (20 mL) and water (20 mL). The reaction mixture was heated at 60 C for 5 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with saturated aqueous sodium bicarbonate solution and was extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 2-bromo-5-fluoroisonicotinaldehyde oxime (1.8 g, 8.22 mmol, 84% yield) as an off-white solid which was carried forward without further purification. LCMS (ESI) m/e 219.0 [(M+H) +, calcd for C6H5BrFN20 219.0]; LC/MS retention time (method Al): tR = 1.63 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1005291-43-9, 2-Bromo-5-fluoroisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53939-30-3, 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.53939-30-3, name is 5-Bromo-2-chloropyridine, molecular formula is C5H3BrClN, molecular weight is 192.44, as common compound, the synthetic route is as follows.

EXAMPLE 2 N-(2,5-difluorobenzyl)-3-[4-(4-methylpiperazin-l-yl)phenyl][l ,2,4]triazolo[4,3-a]pyridin amine5 -Bromo-2-hydrazinylpyridine (2-2) Hydrazine (1,633 mL, 52.0 mmol) was mixed with a stirred, room temperature of 5-bromo-2- chloropyridine (2000 mg, 10.39 mmol) in dioxane (13 mL). The reaction mixture was stirred for 110 C for overnight. The reaction mixture was quenched with aqueous sodium hydrogen carbonate (saturated, 50 mL). The reaction mixture was extracted with EtOAc (3 x 30mL). The combined organic fractions were washed with brine (saturated, 40 mL), dried and filtered. The solvent was evaporated under reduced pressure to provide the title compound; MS (ES) m/z M calc’d; 188, found: 188.

The chemical industry reduces the impact on the environment during synthesis 53939-30-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GREEN, Ahren; LI, Yiwei; STACHEL, Shawn; WO2012/125667; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884495-39-0, 5-Bromo-2-methoxypyridin-3-amine, 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, HPLC of Formula: C6H7BrN2O, blongs to pyridine-derivatives compound. HPLC of Formula: C6H7BrN2O

A mixture of 2,4-difluorobenzenesulfonyl chloride (12.76 g, 60 mmol), pyridine (6 mL, 75 mmol), 5-bromo-2-methoxypyridin-3-amine 15a (10.15 g, 50 mmol), and DMAP (1.22 g, 10 mmol) in DCM (200 mL) was stirred at rt overnight. Water was added and the resulting mixture was extracted with DCM (200 mL×3). The combined organic layers were washed with water (200 mL×2) and brine (30 mL×2), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, PE/EtOAc = 5:1) to afford 16a as a yellow solid (16.48 g, 87% yield). 1H NMR (400 MHz, DMSO-d6) delta 10.46 (s, 1H), 8.13 (d, J = 2.3 Hz, 1H), 7.84 – 7.70 (m, 2H), 7.64 – 7.51 (m, 1H), 7.23 (td, J = 8.5, 2.0 Hz, 1H), 3.61 (s, 3H). MS (ESI+) m/z 379.1 [M + H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884495-39-0, 5-Bromo-2-methoxypyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Article; Lin, Songwen; Wang, Chunyang; Ji, Ming; Wu, Deyu; Lv, Yuanhao; Sheng, Li; Han, Fangbin; Dong, Yi; Zhang, Kehui; Yang, Yakun; Li, Yan; Chen, Xiaoguang; Xu, Heng; Bioorganic and Medicinal Chemistry; vol. 26; 3; (2018); p. 637 – 646;,
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. 132606-40-7, name is 5-Bromo-2-chloro-6-methylpyridine, the common compound, a new synthetic route is introduced below. name: 5-Bromo-2-chloro-6-methylpyridine

To a stirred solution of 3-bromo-6-c oro-2-me1hylpyridine (105 g, 509 mmol) in CCI4 (2 L) was added N-bromosuccinimide (95 g, 534 mmol) followed by AIBN (8.35 g, 50.9 mmol). The reaction was brought to reflux for 24 hours and then cooled to r.t, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 60% methylene chloride heptanes afforded 144.7 g of semi-pure product. Further purification by SFC on a Chiralpak AD-H column with 20% IPA/CO2 [the conditions of the preparative separation were as follows: column Chiralpak AD-H (2.1×25 cm, 5 um particle size) (Chiral Technologies, West Chester, PA, USA); mobile phase 20% 2-propanol/C02; elution mode isocratic pump-mixed; flow rate 50 mL rnin; pressure 100 bar.] gave 3-bromo-2-(bromomethyl)-6-cMoropyridine.LCMS – 285.7 (M+l)+ *H NMR (CDC13> 500 MHz) delta 7.81 (d, J= 8.4 Hz, 1H), 7.15 (d, J= 8.3 Hz, 1H), 4.63 (s, 2H).

The synthetic route of 132606-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; THOMPSON, Christopher, F.; SWEIS, Ramzi, F.; WO2011/28395; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 115473-15-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 115473-15-9 as follows.

A reaction flask equipped with a stirrer, a condenser and a thermometer was charged with Intermediate II-214.9 g,This was dissolved in 40 ml of trichloromethane, 15.0 g of triethylamine was added under stirring,9.5 g of 5,6,7,7a-tetrahydrothieno [3,2-c] pyridin-2 (4H) -one hydrochloride were added portionwise to the reaction system,After completion of the dropwise addition, the reaction was continued at 0 C for 3 hours (the plate showed complete reaction).The reaction solution was washed with 3 x 20 ml of water, the chloroform layer was separated,Dried over anhydrous sodium sulfate, filtered, evaporated to dryness under reduced pressure,To give 12.0 g of a pale yellow solid product (HPLC: 98.9%),

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115473-15-9, its application will become more common.

Reference:
Patent; Tianjin Institute of Pharmaceutical Research; LIU, DENG KE; MU, SHUAI; LIU, YING; NIU, DUAN; TAN, CHU BING; ZHOU, ZHI XING; LIU, CHANG XIAO; (22 pag.)CN103896962; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19733-96-1, 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. 19733-96-1, name is 2-(6-Methylpyridin-3-yl)acetic acid, molecular formula is C8H9NO2, 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 4 Preparation of 2-(6-methylpyridin-3-yl)N-p-tolylamide 2-methylpyridinylacetic acid was dissolved in 150ml of DMF, added with DIEA 40ml, p-toluidine 10.2g, HOBt 18g, and stirred for 15min, then added with EDC.HCl 21g, after addition, the reaction was performed at room temperature for 12h. Then, water 800ml was added for dilution, stirred, insoluble solid appeared, after stirring for 2h, suction filtrated, washed with water to obtain off-white powder solid, dired to obtain 2-(6-methylpyridin-3-yl)N-p-tolylamide 12g, yield was about 68%. 1H-NMR(400MHz,DMSO-d6) delta 2.19(3H,s,CH3); 2.39(3H,s, CH3); 3.56(2H,s, CH2); 7.06-7.04(2H,d, ArH); 7.15-7.17(1H,d, ArH); 7.40-7.42(2H,d, ArH); 7.55-7.57(1H,dd,ArH); 8.32(1H,d,ArH); 10.07(1H,s, NH).

According to the analysis of related databases, 19733-96-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A.; EP2417973; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1658-42-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1658-42-0 as follows.

General procedure: An oven-dried Schlenk tube was charged with Pd(OAc)2 (0.015 mmol, 3.4 mg), X-Phos (0.015 mmol, 7.2 mg), Cs2CO3 (0.9 mmol, 293 mg), substrate 1 (0.3 mmol) and 2 (0.4 mmol). The reaction vessel was evacuated and backfilled again with nitrogen gas, and 1,4-dioxane (1 mL) was added via syringe under nitrogen. The reaction mixture was stirred at 100 C for 12 hours. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The crude was nextfiltered through a plug of celite, which was washed with ethyl acetate. The solution was concentrated and further purifiedby flash column chromatography to afford the corresponding product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1658-42-0, its application will become more common.

Reference:
Article; Jin, Chaochao; Xu, Kun; Fan, Xiao; Liu, Changyao; Tan, Jiajing; Chinese Chemical Letters; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem