Tag: M.W:200-300

Electric Literature of 14529-54-5 ,Some common heterocyclic compound, 14529-54-5, molecular formula is C6H5Br2NO, 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 sealed tube was equipped with a magnetic stirrer and charged with 285b (1.1 g, 6.4 mmol), 3,5-dibromo-l-methylpyridin-2(lH)-one 5 (1.7 g, 6.4 mmol) and cesium carbonate (4.6 g, 14 mmol) in 1,4-dioxane (64 mL). After bubbling nitrogen through the solution for 30 min, Xantphos (440 mg, 0.8 mmol) and tris(dibenzylideneacetone) dipalladium(O) (400 mg, 0.5 mmol) were added, and the reaction mixture was heated to 100 C for 16 h. After this time, water (50 mL) and ethyl acetate (50 mL) were added. The aqueous layer was separated and extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were washed with brine (100 mL) and dried over sodium sulfate. The resulting residue was purified by column chromatography eluting with a gradient of methylene chloride – 60:35:5 methylene chloride: diethyl ether: methanol to afford a 28% yield (620 mg) of 285c.

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. 14529-54-5, 3,5-Dibromo-1-methylpyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1180132-17-5, 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.1180132-17-5, name is 5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine, molecular formula is C12H20N4, molecular weight is 220.31, as common compound, the synthetic route is as follows.

Nitrogen was bubbled into a solution of compound 104 (40 mg, 0.13 mmol, 1.0 eq), compound 8 (30.2 mg, 0.137 mmol, 1.05 eq), Pd2(dba)3 (11.9 mg, 0.013 mmol, 0.1 eq), Xantphos (15 mg, 0.026 mmol, 0.2 eq) and CS2CO3 (84.7 mg, 0.26 mmol, 2.0 eq) in dioxane (2 mL) for 5 mins. The mixture was stirred at 110 C for 2 h. After completion, the mixture was cooled down to RT, the mixture was diluted with DCM (5 mL) and filtered through celite, washed with DCM (4 mL), dried over sodium sulfate, concentrated and purified by pre-HPLC to give the desired product (20 mg, 31%). *H NMR (300 MHz, CDCb): delta 8.40-8.34 (m, 2 H), 8.27 (s, 1 H), 8.23 (s, 1 H), 8.09 (s, 1 H), 7.82 (d, J= 13.5 Hz, 1 H), 7.72 (d, J= 7.8 Hz, 1 H), 4.53 (t, J= 7.2 Hz, 2 H), 3.50 (s, 1 H), 3.32 (t, J= 7.2 Hz, 2 H), 2.88-2.83 (m, 2 H), 2.61-2.43 (m, 10 H), 1.09 (t, J= 6.9 Hz, 3 H). LC-MS (ESI): (M+H)+ = 491.3.

The chemical industry reduces the impact on the environment during synthesis 1180132-17-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BEIJING XUANYI PHARMASCIENCES CO., LTD.; SONG, Yuntao; CHEN, Xiaoqi; (188 pag.)WO2019/35008; (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. 62774-90-7, name is 2,6-Dichloro-4-methylnicotinic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C7H5Cl2NO2

To a solution of 2,6-dichloro-4-methylnicotinic acid (10 g, 48.5 mmol) in DMF (162 mL) was added potassium carbonate (10.06 g, 72.8 mmol) and MeI (12 mL, 192 mmol) at 0 C. The reaction mixture was stirred at RT for 3 h and was subsequently poured into water. This mixture was extracted with EtOAc and the organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material was used without further purification.

The synthetic route of 62774-90-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAO, JIANMING; GAO, XIAOLEI; KNOWLES, SANDRA L.; LI, I, CHUNSING; LO, MICHAEL MAN-CHU; MAZZOLA, Jr., ROBERT D.; ONDEYKA, DEBRA L.; STAMFORD, ANDREW W.; ZHANG, FENGQI; (214 pag.)US2017/183342; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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

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

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

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 875781-15-0, name is 5-Bromo-2-fluoronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H3BrFNO

[00434] 1A. (R,E)-N-((5-Bromo-2-fluoropyridin-3-yl)methylene)-2-methylpropane-2- sulfmamide: To the solution of 5-bromo-2-fluoronicotinaldehyde (5 g, 24.51 mmol), titanium (IV) ethoxide (15.42 ml, 73.5 mmol) in DCM (49.0 ml) was added (R)-2- methylpropane-2-sulfinamide (3.12 g, 25.7 mmol) and the reaction mixture was stirred at rt. After 48 h, the reaction mixture was poured into brine while rapidly stirring to form a suspension. The resulting suspension was filtered through a plug of CELITE, and the filter cake was washed several times with DCM. The filtrate phases were separated, and the organic phase was washed with brine and dried over MgS04. The organic layers were then concentrated to give 7.6 g crude product which was further purified using silica gel chromatography to yield the desired product (6.97 g, 93%) as an off white solid. MS(ESI) m/z: 330.8 (M+Na)+.

With the rapid development of chemical substances, we look forward to future research findings about 875781-15-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 82671-06-5 , The common heterocyclic compound, 82671-06-5, name is 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid, molecular formula is C6H2Cl2FNO2, 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.

Intermediate[00144] The overall synthetic scheme for the synthesis of5-fluoro-lH-pyrazolo [3, 4-b] pyridin-3-amine 5 is depicted below.1 6 3Reagents and conditions: i. Pd (OAc) 2, PPh3, Et3N, H2CO2; ii. 1) (COCl)2, CH2Cl2, cat. DMF; 2) NH3 (g) , dioxane, iii. TFAA, Et3N, CH2Cl2, 0C; iv. H2NNH2. H2O, n-butanol, reflux2-Chloro-5-fluoronicotinic acid (6)[00145] To a round-bottomed flask under a N2 atmosphere were added degassed DMF (270 ?iL) , Pd(OAc)2 (0.05 eq, 2.7 g, 11.9 mmol) , PPh3 (0.1 eq, 6.2 g, 23.8 mmol) , and degassed Et3N (6 eq, 200 mL, 1428.6 mmol) . The mixture was stirred for 20 minutes, HCOOH (3 eq, 28 mL, 714.3 mmol) was then added. 5 minutes later, 2, 6-dichloro-5-fluoronicotinic acid (50 g, 238.1 mmol) was added. The mixture was stirred at 500C. The reaction was followed by analysis (IH NMR) of a worked- up aliquot. When all starting material was consumed (24 h) , the mixture was cooled to 00C and water (500 mL) was added. After 20 minutes, The mixture was filtered through a pad of Celite that was rinsed with water. The mixture was basified to pH 9 with 30% aq. NaOH and washed with EtOAc (2x) . HCl(12 N) was added slowly to pH 1 and the solution was saturated with NaCl. The mixture was extracted with EtOAc (3x) . The combined organic extracts were washed with brine, dried (Na2SO4) , and concentrated under reduced pressure to give 37 g (88%) of a beige solid used in the next step without further purification. 1H NMR (DMSO-de, 300 MHz): delta 8.16 (dd, IH); 8.58 (d, IH).

The synthetic route of 82671-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/112646; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem