Category: pyridine-derivatives

Electric Literature of 92992-85-3, 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. 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. A new synthetic method of this compound is introduced below.

To a mixture of (R)-2-methylpiperazine-1-carboxylic acid tert-butyl ester (1 g),2-bromo-3,5-dimethylpyridine (975 mg),tris(dibenzylideneacetone)dipalladium(O)(92 mg),rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (125 mg) and tert-butoxy sodium (650 mg) was added toluene (17 mL) and the mixture was stirred under microwave irradiation at 130c for 2 hr. The reaction mixture was purified by column chromatography (hexane:ethyl acetate)to give the title compound (220 mg). MS (ESI)m/z: 306(M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92992-85-3, 2-Bromo-3,5-dimethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 137778-20-2, 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 137778-20-2, name is 5-Bromo-6-methylpicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 10Methyl 5-bromo-6-methyl-2-pyridine carbonate synthesisInto a 500-l. glass-lined reactor was placed 5-bromo-6-methyl-2-pyridine carboxylic acid (30 kg, 138.9 moles) and methanol (133 kg, 4156 moles). The mixture was agitated and thionyl chloride (36.8 kg, 309.2 moles) was added while the temperature was maintained between 2030 C. After the addition, the mixture was heated to 5565 C. for 2 hrs. The reaction was stopped when the raw material was detected at less than 2%. Then solvent was removed by concentration at a temperature below 40 C. MTBE (280 kg) was added and the mixture was stirred for another 30 min. to dissolve the crude. Then the MTBE solution was transferred to one drum. To the above reactor was added water (300 kg). Then the solution containing the crude was pumped to the reactor while maintaining the reactor contents at 05 C. and stirred for 1 hr. After phase separation, the aqueous layer was extracted with MTBE (60 kg). The organic phases were combined, and concentrated at a temperature below 40 C. Hexane (60 kg) was added to the residue. The obtained solid was stirred, centrifuged and dried. White powder (22.36 kg, 97.2 moles) was obtained. The purity of the product was >98%, and the mole yield was 70%.

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 137778-20-2, 5-Bromo-6-methylpicolinic acid.

Reference:
Patent; Synergetica Changzhou Chemical Company; US2010/305330; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131747-55-2, Adding some certain compound to certain chemical reactions, such as: 131747-55-2, name is 2-Fluoro-3-(hydroxymethyl)pyridine,molecular formula is C6H6FNO, 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 131747-55-2.

At 0C, 55% sodium hydride 0.70 g (16 mmol) was added in portions to a THF (20 mL) solution of (2-fluoropyridin-3-yl)methanol 1.3 g (10 mmol) synthesized in the same manner as in Reference Example 52 and iodomethane 6.6 mL (110 mmol), and the mixture was stirred at room temperature for 2 hours. After the completion of the reaction, water was added to the reaction mixture, and followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (eluting solvent: hexane:ethyl acetate) to give the title compound 0.89 g (6.3 mmol, yield 63%) as a colorless oil. 1H-NMR spectrum (400MHz, DMSO-d6) delta:8.23 – 8.14 (m, 1H), 8.02 – 7.92 (m, 1H), 7.40 – 7.35 (m, 1H), 4.46 (s, 2H), 3.33 (s, 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. 131747-55-2, 2-Fluoro-3-(hydroxymethyl)pyridine, other downstream synthetic routes, hurry up and to see.

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

Related Products of 1235036-15-3 , The common heterocyclic compound, 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate, molecular formula is C10H11BrClNO2, 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 7A methyl 2-(5-bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate A solution of methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate (1.00 g), EXAMPLE 1C (1.68 g) and cesium carbonate (2.56 g) was stirred together in N,N-dimethylacetamide (10 mL) at 110 C. overnight. The reaction was cooled, diluted with ethyl acetate (50 mL) and washed with water (2*25 mL) and brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography using 1-30% ethyl acetate in hexanes provided the title compound.

The synthetic route of 1235036-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Wang, Le; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96121; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 880870-13-3 ,Some common heterocyclic compound, 880870-13-3, molecular formula is C6H5BrClNO, 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 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 for 12 h under nitrogen atm. The reaction mixture was cooled to ambient temperature, filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30 ethyl acetate/hexanes to afford the product. 1H NMR (500 MHz, DMSO-d6) , delta 8.69 (s, 1H) , 7.50 (s, 1H) , 4.04 (s, 3H) LC/MS (M+1) + 169.

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.; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; SHI, Zhi-Cai; WALSH, Shawn P.; WU, Zhicai; YU, Yang; FERGUSON II, Ronald; GUO, Zhiqiang; FRIE, Jessica; SUZUKI, Takao; BLIZZARD, Timothy A.; FU, Qinghong; VANGELDER, Kelsey F.; (118 pag.)WO2016/65582; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 688782-02-7, 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. 688782-02-7, name is 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7ClN2, 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 97(1)4-Chloro-3-methyl-1-{(2-(trimethylsilyl)ethoxy)methyl}-1H-pyrrolo[2,3-b]pyridine (97a)Compound (40d) (1.0 g) was dissolved in DMF (20 mL), and sodium hydride (0.288 g, a 55% dispersion in paraffin liquid) was added to the resulting solution at 0 C., followed by stirring for 10 min. Then, {2-(chloromethoxy)ethyl}silane (1.16 mL) was added to the reaction solution, followed by stirring at room temperature for 1 hr. Ice water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and was then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate) to obtain compound (97a) (4.50 g, 84%) as a colorless oily substance.1H-NMR (CDCl3) delta: 8.21 (1H, d, J=5.12 Hz), 7.19 (1H, s), 7.10 (1H, d, J=5.12 Hz), 5.68 (2H, s), 3.58 (2H, t, J=8.17 Hz), 2.43 (3H, s), 0.97 (2H, t, J=8.17 Hz), 0.00 (9H, s); LRMS (ESI) m/z 297 [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 688782-02-7, 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; US2012/108589; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 178876-83-0 , The common heterocyclic compound, 178876-83-0, name is Methyl 6-amino-3-bromopicolinate, molecular formula is C7H7BrN2O2, 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 solution of methyl 6-amino-3-bromopicolinate (200 mg, 866 umol, 1 eq) in EtOH (50 mL) was added NaHC03 (124 mg, 1.47 mmol, 1.7 eq) and l-chloropropan-2- one (2.35 g, 25.4 mmol, 3.00 mL, 29.3 eq). The reaction was stirred at 90 C for 24 hr. The reaction was cooled to 25 C and concentrated in vacuo. To the residue was added water (50 mL). The aqueous phase was extracted with ethyl acetate (50 mL*3). The combined organic phase was washed with brine (50 mL*2), dried with anhydrous Na2S04, filtered and (0369) concentrated in vacuo. The residue was purified by Prep-TLC (Petroleum ether/Ethyl acetate=l/l). Example 1 14A (120 mg crude) was obtained as a brown oil. ESI m/z 269[M +1 ]+.

The synthetic route of 178876-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHRYSALIS, INC.; GWALTNEY, Stephen; (147 pag.)WO2017/214413; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 10273-89-9, name is 2-(o-tolyl)pyridine, molecular formula is C12H11N, 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. Recommanded Product: 10273-89-9

General procedure: Unless otherwise stated, in an Argon filled glove-box a crimp-cap microwave vial equipped with a magnetic stirring bar was charged with the appropriate cyclometalated Ru(ll)-catalyst (like Ru1-Ru46, from 3 mol % to 10 mol %), KOAc (5.9 mg, 0.06 mmol, 30 mol %), K2CO3 (2.0 – 4.0 equiv.), the appropriate DG-containing arene (like N1-N12, 0.20 mmol, 1.0 equiv.), the appropriate (hetero)aryl (pseudo)halide (like X1-X42, 0.2 mmol, 1.0 equiv) and /V-methyl-2- pyrrolidone (NMP) (200 pL, 1 M). The vial was capped and stirred at 35 C for 24 hours. Upon completion, the crude mixture was loaded on a silica gel column and purified by flash chromatography.

With the rapid development of chemical substances, we look forward to future research findings about 10273-89-9.

Reference:
Patent; THE UNIVERSITY OF MANCHESTER; LARROSA, Igor; SIMONETTI, Marco; CANNAS, Diego Maria; (94 pag.)WO2019/215426; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19235-89-3 ,Some common heterocyclic compound, 19235-89-3, molecular formula is C6H3ClN2, 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-Acetyl-4-chloropyridine: To a solution of 4-chloro-2-pyridinecarbonitrile (5.35 g, 38.6 mmol) in benzene (50 ml) and ether (50 ml) cooled to 0 C was added dropwise over 20 min a 2M solution of MeMgI in ether (23 ml, 46.3 mmol). After 0.5 h, the mixture was allowed to warm to ambient temperature, and stirring continued for 2 hours. The mixture was cooled to 0 C and 2M aqueous HCl (100 ml) added. Themixture was made basic with saturated aqueous sodium bicarbonate (~80 ml) and the organic layer separated and dried (MgSO4). After removal of solvent, the residue was purified by flash chromatography eluding with ethyl acetate/hexane (1:5) to afford 3.60 g (60%) of 2-acetyl-4-chloropyridine. 1H-NMR (DMSO-d6) 8.59 (1 H, d, J=5.1 Hz), 8.04 (1 H, d, J=1.8 Hz), 7.47 (1 H, dd, J=1.8, 5.1 Hz), 2.72 (3 H, s).

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. 19235-89-3, 4-Chloropyridine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; EP1065206; (2001); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 905563-79-3, 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. 905563-79-3, name is 2-Chloro-4-methoxynicotinaldehyde, molecular formula is C7H6ClNO2, 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.

Step 2: 2-Chloro-4-methoxypyridin-3-yl)methanol (26) A solution of 2-chloro-4-methoxynicotinaldehyde (0.190 g, 1.11 mmol) in methanol (10 mL) was treated with sodium borohydride (0.044 g, 1.2 mmol) and stirred at RT for 1 hour. The reaction was concentrated in vacuo, redissolved in ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered and concentrated, providing the crude title compound which was used without further purification. LRMS m/z (M+H) 174.2 found, 174.1 required.

According to the analysis of related databases, 905563-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2014/176144; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem