Tag: M.W:200-300

Reference of 131803-48-0, 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. 131803-48-0, name is Methyl 6-(bromomethyl)nicotinate, molecular formula is C8H8BrNO2, 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.

Methyl 6-(anilinomethyl)pyridine-3-carboxylate hydrochloride (I-30) A mixture of N-Boc-aniline (350 mg, 1.81 mmol) and methyl 6-(bromomethyl)pyridine-3-carboxylate (500 mg, 2.17 mmol) in THF (10 mL) at 0 C. was added with sodium hydride (108 mg, 60% dispersion in mineral oil, 2.71 mmol). The reaction was stirred for 1 h at room temperature was then heated at 60 C. for 5 h. The reaction was cooled to room temperature and quenched with water. The mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic phase was washed with brine, dried over MgSO4 then evaporated to dryness. The residue was taken up with 4N solution of HCl in dioxane (5.5 mL) and the resulting mixture was stirred at room temperature for 2 h. The reaction was concentrated under reduced pressure and the residue was triturated with diethyl ether to provide the title compound (394 mg, 78%) as an off-white solid. 1H NMR (400 MHz, DMSO): delta 9.07 (d, J=2.0 Hz, 1H), 8.33 (dd, J=2.0, 8.0 Hz, 1H), 7.59 (d, J=8.4 Hz, 1H), 7.14-7.10 (m, 2H), 6.74-6.70 (m, 3H), 4.54 (s, 2H), 3.88 (s, 3H), NH not observed.

According to the analysis of related databases, 131803-48-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; ARMANI, Elisabetta; GHIDINI, Eleonora; BAKER-GLENN, Charles; VAN DE POEL, Herve; WHITTAKER, Ben; US2015/158858; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1152617-24-7 ,Some common heterocyclic compound, 1152617-24-7, molecular formula is C5H4ClIN2, 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.

To a mixture of Z l7c (6.95 kg, assay 72%, 27.23 mol) in l,4-dioxane (72 L) was added Xantphos (233 g, 41 1 mmol, 0.015 eq), Pd2(dba)3 (186 g, 206 mmol,0.0075eq), Z l7b (7.13 kg, 28.02 mol) and DIPEA (7.02 kg, 54.46mol). The system was vacuated and purged with nitrogen gas three times. The mixture was stirred at 65 C for 16 h under N2. The mixture was cooled to rt and water (50 L) was added, filtered. The cake was washed with EA (25L). The filtrate was extracted with EA (4 x 20 L). The organic phase was concentrated in vacuum to offer the crude product which was combined with the cake. Then DCM (60 L) was added to the crude product and stirred at 25-30C for 18h and then filtered. The filter cake was slurried with CH2CI2 (30 L) for 4 hrs and filtered. The filter cake was slurred in CH2CI2 (30 L) for 16 hrs and filtered. Then the filter cake was dried in vacuum to give Z17a (9.1 kg, 84 %) as light yellow solid. NMR (400 MHz, DMSO-d6)5 = 7.89 (s, 1H), 7.7 (d, J = 7.6 Hz, 1H), 7.18 (bs, 2H), 6.40 (bs, 2H), 5.97 (d, J = 7.6 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1152617-24-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; ZHANG, Hao; JIA, Huanqing; WANG, Hui; WANG, Jianhua; LI, Wei; LIN, Xiaohui; MIN, Zhongcheng; (91 pag.)WO2020/65452; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84487-10-5, Adding some certain compound to certain chemical reactions, such as: 84487-10-5, name is 2-Amino-4-bromo-3-nitropyridine,molecular formula is C5H4BrN3O2, 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 84487-10-5.

Step 1 (0852) A solution of 4-bromo-3-nitropyridin-2-amine (LXVI) (5.00 g, 22.9 mmol, 1.00 eq), (2-fluorophenyl)boronic acid (LXVII) (3.82 g, 27.5 mmol, 1.20 eq), Pd(PPh3)4 (1.32 g, 1.14 mmol, 0.05 eq), and Na2CO3 (4.85 g, 45.8 mmol, 2 eq) in a mixture of toluene (25 mL), H2O (9 mL) and EtOH (6 mL) was stirred at 75 C. for 15 h under nitrogen atmosphere. The reaction mixture was the washed with brine (50 mL) and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resultant residue was purified by chromatography on silica gel (PE:EtOAc=3:1) to give 4-(2-fluorophenyl)-3-nitropyridin-2-amine (LXVIII) (4.0 g, 17.15 mmol, 74.9%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta ppm 6.29 (brs, 2H), 6.68 (d, J=4.8 Hz, 1H), 7.14 (t, J=5.2 Hz, 1H), 7.23-7.50 (m, 3H), 8.32 (d, J=4.8 Hz, 1H); ESIMS found C11H8FN3O2 m/z 234.2 (M+H).

According to the analysis of related databases, 84487-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68551; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65001-21-0 ,Some common heterocyclic compound, 65001-21-0, molecular formula is C5H3BrClNO2S, 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.

Example 36A tert-Butyl 4-{[(5-bromopyridin-3-yl) sulphonyl]amino}piperidine-1-carboxylate 5-Bromopyridine-3-sulphonyl chloride (1 g, 3.9 mmol) was dissolved in dichloromethane (20 ml), the mixture was cooled to 0 C. and tert-butyl 4-aminopiperidine-1-carboxylate (1.18 g, 5.8 mmol) and N,N-diisopropylethylamine (1.7 ml, 9.7 mmol) were added. The reaction mixture was stirred at RT overnight and concentrated, and the residue was purified chromatographically by HPLC (Method 9). This gave 1.0 g (62% of theory) of the title compound. 1H NMR (300 MHz, DMSO-d6): delta=ppm 1.09-1.24 (m, 2H), 1.33 (s, 9H), 1.47-1.59 (m, 2H), 2.66-2.83 (m, 2H), 3.19-3.25 (m, 1H), 3.63-3.75 (m, 2H), 8.09 (br. s, 1H), 8.36 (t, 1H), 8.91 (d, 1H), 8.95 (d, 1H). LC-MS (Method 4): Rt=1.19 min; MS (ESIneg): m/z=420.3 [M-H]-.

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. 65001-21-0, 5-Bromopyridine-3-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHN, Ulrike; ELLERMANN, Manuel; STRASSBURGER, Julia; WENDT, Astrid; ROeHRIG, Susanne; WEBSTER, Robert Alan; SCHMIDT, Martina Victoria; TERSTEEGEN, Adrian; BEYER, Kristin; SCHAeFER, Martina; BUCHMUeLLER, Anja; GERDES, Christoph; SPERZEL, Michael; SANDMANN, Steffen; HEITMEIER, Stefan; HILLISCH, Alexander; ACKERSTAFF, Jens; TERJUNG, Carsten; (163 pag.)US2016/244437; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 38185-56-7, 5-Bromo-3-chloro-2-fluoropyridine, 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, Recommanded Product: 38185-56-7, blongs to pyridine-derivatives compound. Recommanded Product: 38185-56-7

STEP-1 : 5 -BROMO-3 -CHLORO-2-ISOBUTOXYP YRIDINE[00214] To a solution of 5-bromo-3-chloro-2-fluoropyridine (5.0 g, 23.7 mmol, LLB Chem) and 2-methylpropan-l-ol (5.28 g, 71.3 mmol, Spectrochem) in DMSO (100 mL) was added CS2CO3(23.0 g, 71.3 mmol, GLR) and the reaction was heated at 90 C for 3 h. The reaction mixture was allowed to cool to room temperature, water (500 mL) was added and the aqueous layer was extracted with diethyl ether (2 x 500 mL). The combined organic extract was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by column chromatography (silica gel 100-200 mesh and 0-5% ethyl acetate in hexanes) to obtain compound-3 (5.0 g, 86%) as colorless oil. TLC solvent system: 10% ethyl acetate in hexanes, product’s Rf: 0.8. MS (ESI, positive ion): No ionization.1H NMR (400 MHz, CDC13) delta 8.06 (d, J= 2.2 Hz, 1H), 7.74 (d, J= 2.2 Hz, 1H), 4.11 (d, J= 6.7 Hz, 2H), 2.12 (dp, J= 13.4, 6.7 Hz, 1H), 1.03 (d, J= 6.7 Hz, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38185-56-7, 5-Bromo-3-chloro-2-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; CHAKKA, Nagasree; DIMAURO, Erin F.; GAO, Hua; GUNAYDIN, Hakan; HUANG, Hongbing; OLIVIERI, Philip; SCHENKEL, Laurie; WEISS, Matthew; WO2015/51043; (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 69045-84-7, name is 2,3-Dichloro-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H2Cl2F3N

The synthetic route of title compounds was outlined in Scheme (1). 2,3-Dichloro-5-(trifluoromethyl)pyridine (7.50mmol) was dissolved in ethanol (300 mL), then hydrazine hydrate (30 mmol) was dropwised under refluxing condition for 72 h to give 3-chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine 1. A CEM designed 10 mL pressure-rated vial was charged with 3-chloro-2-hydrazinyl-5-(trifluoromethyl) pyridine 1 (211 mg, 1 mmol) and aldehyde (1mmol), HOAc (0.1 mmol) in the solution of ethanol at the condition of microwave (15 min, 85C). All the other compounds are synthesized according the procedure.

With the rapid development of chemical substances, we look forward to future research findings about 69045-84-7.

Reference:
Article; Min, Li-Jing; Shi, Yan-Xia; Yang, Ming-Yan; Zhai, Zhi-Wen; Weng, Jian-Quan; Tan, Cheng-Xia; Liu, Xing-Hai; Li, Bao-Ju; Zhang, Yong-Gang; Letters in drug design and discovery; vol. 13; 4; (2016); p. 324 – 328;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 137640-84-7, 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. 137640-84-7, name is 6-(3-(Trifluoromethyl)phenoxy)picolinic acid. A new synthetic method of this compound is introduced below.

EXAMPLE 24 Preparation of N-(2,4-difluorophenyl)-2-(3-alpha,alpha,alpha-trifluoromethylphenoxy)-6-pyridinecarboxamide 6-(3-alpha,alpha,alpha-Trifluoromethylphenoxy)picolinic acid (7.1 g) in thionyl chloride (50 ml) was refluxed for 1 hour. The excess thionyl chloride was evaporated in vacuo and dichloromethane added to the residual picolinoyl chloride. A solution of 2,4-difluoroaniline (3.3 g) and triethylamine (2.6 g) in dichloromethane (50 ml) was then added dropwise with stirring at ambient temperature. After stirring a further 1 hour, the reaction mixture was washed with water, dried over anhydrous magnesium sulphate and the dichloromethane evaporated. The residue was purified on a silica gel column using dichloromethane as eluant to give the title compound (6.9 g) as a white solid of melting point 110-111 C. m/e Theory: Found 394:394

At the same time, in my other blogs, there are other synthetic methods of this type of compound,137640-84-7, 6-(3-(Trifluoromethyl)phenoxy)picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Shell Research Limited; US5294597; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 874959-68-9 , The common heterocyclic compound, 874959-68-9, name is 5-Bromopyridine-2-sulfonyl chloride, molecular formula is C5H3BrClNO2S, 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.

Example 58(a) l-(5-Bromo-pyridine-2-sulfonyl)-4-methyl-piperazine; 5-Bromopyridine-2-sulfonyl chloride (as described in Example 52(b) (55.0 mg, 0.214 mmol) was dissolved in CH2Cl2 (1 mL) and 1-methyl-piperazine (26 muL, 0.236 mmol) was added. Stirring was continued at room temperature for 3 hours and saturated aqueous NaHCO3 (1 mL) was added. The mixture was diluted with CH2Cl2 (5 mL) and the aqueous phase was extracted with CH2Cl2 (3 x 5 mL). The combined organic phases were dried (Na2SO4) and concentrated to afford the title compound (61 mg, 89%). 1H NMR (400 MHz, CDCl3) delta ppm 2.29 (s, 3 H) 2.33 – 2.38 (m, 2 H) 2.45 – 2.50 (m, 2 H) 3.10 – 3.18 (m, 2 H) 3.30 – 3.37 (m, 2 H) 7.31 (d, J=4.29 Hz, 1 H) 7.81 (d, J=7.58 Hz, 1 H) 8.04 (dd, J=8.34, 2.27 Hz, 1 H); MS (ESI) m/z 321 (M + 1).

The synthetic route of 874959-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/2244; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 80194-68-9, 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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid. A new synthetic method of this compound is introduced below.

A mixture of 2-amino-4-(trifluoromethylsulfanyl)phenol 1.0 g, 3-chloro-5-trifluoromethylpicolinic acid 1.08 g, EDC hydrochloride 1.10 g, and chloroform 10 mL was stirred at RT for 1 hr. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 3-chloro-5-trifluoromethyl-N-[2-hydroxy-5-(trifluoromethylsulfanyl)phenyl]picolinamide 1.94 g. 3-chloro-5-trifluoromethyl-N-[2-hydroxy-5-(trifluoromethylsulfanyl)phenyl]picolinamide 1H-NMR(CDCl3)delta: 8.78(1H, d), 8.15(1H, d), 8.09(1H, d), 7.37(1H, dd), 7.04(1H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Chemical Company, Limited; SHIMIZU, Chie; KAMEZAKI, Masashi; NOKURA, Yoshihiko; EP2952098; (2015); 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. 84487-10-5, name is 2-Amino-4-bromo-3-nitropyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 84487-10-5

2-Amino-3-nitro-4-bromopyridine (1 g, 4.59 mmol)Dissolved in 20 ml of 95% ethanol, added stannous chloride(2.61 g, 13.76 mmol).The reaction solution was warmed to reflux and stirred at this temperature for 2-3 hours.Pour the reaction solution into 80 ml of 1N sodium hydroxide solution.Extracted with ethyl acetate (30 mL×3), and the extract was washed with brine.Dry over anhydrous sodium sulfate,Concentrated to a crude product.The crude product was subjected to silica gel column chromatography ( petroleum ether / ethyl acetate = 5:1)2,3-diamino-4-bromopyridine(322 mg, yield 37%)

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, 84487-10-5, 2-Amino-4-bromo-3-nitropyridine.

Reference:
Patent; Shanghai Jiao Tong University; Wang Yongxiang; Fu Lei; Xie Dongsheng; Lu Jun; (37 pag.)CN103435561; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem