Day: May 13, 2021

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 633328-33-3, name is 3-Bromo-1H-pyrazolo[4,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrN3

Example i-2: Preparation of 3-bromo-1H-pyrazolo[4,3-b]pyridine Step 1. Preparation of (3-bromo-1H-pyrazolo[4,3-b]pyridin-1-yl)(2-chloro-6- (trifluoromethyl)phenyl)methanone (i-2). To a flask was added 3-bromo-lH-pyrazolo[4,3-b]pyridine (i-2a) (3.2 g, 16.2 mmol), 2- chloro-6-(trifluoromethyl)benzoyl chloride 2 (3.9 g, 16.2 mmol), DMAP (1.97 g, 16.2 mmol) and DCM (60 mL), followed by the addition of TEA (3.26 g, 32.4 mmol) slowly. The reaction mixture was stirred at 40C for 3h. The mixture was diluted with H20, and the organic layer was separated. The aqueous layer was extracted with CH2C12 . The combined organics were washed with H20, brine, dried over Na2S04, and concentrated. The residue was purified by flash chromatography (Petroleum/EtOAc, 5/1) to afford 3.0 g (46%) of the title compound. LCMS (ESI) calc’d for Ci4H6BrClF3N30 [M+H]+: 406, found: 406.

With the rapid development of chemical substances, we look forward to future research findings about 633328-33-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26328; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 39856-50-3, 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.39856-50-3, name is 5-Bromo-2-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.

To a solution of compound (1) (20.00 g, 98.53 mmol, 1.00 eq) in dimethyl sulfoxide (52 mL), compound (2) (24.00 g, 128.86 mmol, 1.31 eq) and triethylamine (20.00 g, 197.65 mmol, 2.01 eq) were added. The solution was heated to 60 C. and stirred for 18 hours. TLC (petroleum ether:ethyl acetate=3:1) showed the completion of the reaction. The solution was diluted with water (200 mL), stirred for 30 minutes, and then filtered. The filter cake was washed with water and dried under vacuum to obtain a crude product. The crude product was purified by a silica gel column (petroleum ether:ethyl acetate=50:1 to 20:1) to obtain compound (3) (27.00 g, 87.57 mmol, yield: 88.87%). 1H NMR (400 MHz, CDCl3) delta8.18 (d, J=9.03 Hz, 1H), 8.13 (d, J=2.89 Hz, 1H), 7.21 (dd, J=9.10, 2.95 Hz, 1H), 3.69-3.59 (m, 4H), 3.51-3.40 (m, 4H), 1.49 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 39856-50-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Ding, Charles Z.; Chen, Shuhui; Hu, Lihong; Xu, Zhaobing; Liu, Yingchun; Ren, Bingjie; Li, Weidong; Li, Zongbin; Zhao, Rui; Zhang, Xiquan; (21 pag.)US2019/194168; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55717-45-8, 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.55717-45-8, name is 6-Bromopyridin-3-ol, molecular formula is C5H4BrNO, molecular weight is 173.9954, as common compound, the synthetic route is as follows.

Compound (II-3) (5.00 g, 28.7 mmol) was dissolved in DMF (30 mL), potassium carbonate (7.94 g, 57.5 mmol),benzyl bromide (4.1 mL, 35 mmol) and TBAI (531 mg, 1.44 mmol) were added under ice-cooling, and the mixture waswarmed to room temperature and stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extractedwith ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydroussodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gelcolumn chromatography (n-hexane:ethyl acetate = 97:3 ?80:20) to give compound (M-16) (yield 6.97 g, 92%) as awhite solid

Statistics shows that 55717-45-8 is playing an increasingly important role. we look forward to future research findings about 6-Bromopyridin-3-ol.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below., name: 3-Iodo-1H-pyrazolo[3,4-b]pyridine

Add 400 g (1.63 mol, 1.0 eq) of 3-iodo-1H-pyrazolo[3,4-b]pyridine, 369 g (1.96 mol, 1.2 eq) of o-fluorobenzyl bromide and 450 g (3.27 mol, 1.5 eq) of K2CO3 dissolved in 4L of DMF into a 5L 4-neck flask and react for 10 h at room temperature. Pour the reaction solution into water after thorough reaction as monitored by TLC, stir it to appear a plenty of grey solid, filter and recrystallize PE: EA=5:1 to obtain 411 g of light yellow solid. The yield is 71.16%. [0025] 11 H NMR (400 MHz, CDCl3) delta (ppm): 8.62 (d, 1H), 7.85 (d, 1H), 7.27 (dd, 1H), 7.11 (dd, 1H); 6.96-7.08 m, 3H), 5.82 (s, 2H).

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, 117007-52-0, 3-Iodo-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; Pharmablock (Nanjing) R&D Co., Ltd.; Li, Jin; Yang, Xiaoyu; Zhu, Jingwei; Yang, Minmin; Wu, Xihan; US2014/309425; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 126053-15-4, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol, 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, Formula: C8H8ClNO, blongs to pyridine-derivatives compound. Formula: C8H8ClNO

A mixture of intermediate 4 (0.0003 mol) and 4-chloro-6,7-dihydro- 5H- cyclopenta[b]pyridin-7-ol (0.0003 mol) was stirred at 1500C for 20 minutes, cooled to room temperature, extracted with NaHCOs/DCM/methanol (few drops). The organic layers were combined, dried over MgSO4, filtered off and the solvent was evaporated. The residue (0.174g) was purified by column chromatography over silica gel (DCM/methanol 95/5, 93/7 to 90/1 ). The pure fraction was collected and the solvent was evaporated, yielding 0.097 g (68%) of compound 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,126053-15-4, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/37343; (2009); 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 174669-74-0, name is 2-Fluoropyridin-3-ol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H4FNO

Iodomethane 1.7 mL (27 mmol) and cesium carbonate 4.3 g (13. mmol) were added to a DMSO (20 mL) solution of 2-fluoropyridin-3-ol 1.0 g (8.8 mmol), and the mixture was stirred at 60C for 1 hour. After the completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound 1.1 g (8.7 mmol, yield 99%) as a white solid. 1H-NMR spectrum (400MHz, DMSO-d6) delta:7.76 – 7.69 (m, 1H), 7.65 (ddd, J = 1.5, 8.0, 10.7 Hz, 1H), 7.31 (ddd, J = 0.9, 4.8, 8.0 Hz, 1H), 3.88 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 174669-74-0.

Reference:
Patent; UBE Industries, Ltd.; KOMORI, Ken-ichi; NINOMIYA, Akishi; USHIYAMA, Shigeru; SHINOHARA, Masaru; ITO, Koji; KAWAGUCHI, Tetsuo; TOKUNAGA, Yasunori; KAWADA, Hiroyoshi; YAMADA, Haruka; SHIRAISHI, Yusuke; KOJIMA, Masahiro; ITO, Masaaki; KIMURA, Tomio; (432 pag.)EP3333163; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 143150-92-9, 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, 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-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, blongs to pyridine-derivatives compound. Safety of 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

[Referential Example 13] Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridine-2-carboxylate: 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine (531 mg) was dissolved in absolute diethyl ether (20 ml), n-butyllithium (1.54N hexane solution, 1.63 ml) was added dropwise at -78C, and the mixture was stirred for 30 minutes with ice cooling. After passing carbon dioxide into the reaction mixture at -78C for 1 hour, the mixture was warmed to room temperature. The reaction mixture was concentrated under reduced pressure to obtain the title compound (523 mg) as a pale brown solid. 1H-NMR (DMSO-d6) delta: 2.37(3H,s), 2.64-2.77(4H,m), 3.54(2H,s) MS (FAB) m/z: 199(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,143150-92-9, 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1270557; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 103-74-2, 2-(2-Hydroxyethyl)pyridine, 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: C7H9NO, blongs to pyridine-derivatives compound. HPLC of Formula: C7H9NO

General procedure: To a solution of A1B1 (1.0mmol) and triphenylphosphine (1.5mmol) in anhydrous tetrahydrofuran (3mL), added C1 or C2 (2.0mmol) and dropwise added diethyl azodicarboxylate (DEAD, 1.5mmol) in anhydrous and anoxybiotic conditions. The reaction mixture was stirred at-2C for 30min, and then stirred at room temperature for 24h. After completion of reaction was monitored through TLC, the reaction mixture was filtered and washed with ether and saturated salt water to get products because there would be a solid precipitate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103-74-2, 2-(2-Hydroxyethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Article; Wang, Fang; Sun, Jun-Rong; Huang, Mei-Yan; Wang, Hui-Ying; Sun, Ping-Hua; Lin, Jing; Chen, Wei-Min; European Journal of Medicinal Chemistry; vol. 72; (2014); p. 35 – 45;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 106651-81-4 ,Some common heterocyclic compound, 106651-81-4, molecular formula is C7H9Cl2N, 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.

2-(2-Methoxycarbonylethyl)adenine (313 mg, 1.51 mmol) obtained by Reference example 22 and potassium carbonate (0.44 g, 3.18 mmol) were added to DMF (40 ml). The mixture was at 70C for 1 hour and then cooled to room temperature. Thereto was added 6-methyl-3-pyridylmethyl chloride hydrochloride (0.38 g, 2.13 mmol) and the mixture was stirred at room temperature for 15 hours. After removing the solvent, the residue was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (SiO2 20g, eluting solvent: CHCl3/MeOH = 100/1 ~ 30/ 1) to give the captioned compound (358 mg, 1.15 mmol) as a white solid.

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. 106651-81-4, 5-(Chloromethyl)-2-methylpyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1550662; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 99163-12-9 ,Some common heterocyclic compound, 99163-12-9, molecular formula is C12H9NO, 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.

General procedure: Respective aromatic/hetro aromatic aldehydes (6a-r) (0.43 mmol) was added to a pre-mixed solution of compound 5 (0.43 mmol) in ethanol. The reaction content was refluxed for 0.5 h. The solids was filtered and rinsed with ethanol and dried to afford the respective hydrazone derivatives (7a-r) in 82-93 % yield (Scheme-I).

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. 99163-12-9, 4-Pyridin-4-yl-benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sree Lakshmana Rao; Basaveswara Rao, Mandava V.; Prasad; Asian Journal of Chemistry; vol. 31; 3; (2019); p. 627 – 632;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem