Month: April 2022

Electric Literature of 6854-07-5, 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. 6854-07-5, name is 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, molecular formula is C6H4N2O5, 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.

b) 2-Chloro-5-nitro-nicotinic acid 2-Hydroxy-5-nitro-nicotinic acid (2.7 mmol) in a mixture of NJV- dimethylformamide (2.7 mmol) and thionyl chloride (5 ml) was heated at 80 0C for 1 h. The mixture was allowed to cool and concentrated in vacuo. To the resulting residue was added ice-water (20 ml) and with vigorous stirring a precipitate formed. The precipitate was filtered off and dried in a vacuum oven to give a white solid (68%).ESIMS: M-I: found 201 ; expected 201; and1H NMR (300 MHz, DMSO) ? 9.30 (IH, d, H-4), 8.83 (IH, d, H-6).

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 6854-07-5, 5-Nitro-2-oxo-3-pyridinecarboxylic Acid.

Reference:
Patent; BIONOMICS LIMITED; WO2008/46135; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 98121-41-6, 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 98121-41-6, name is 3-Amino-5,6-dichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A 5L flask with mechanical stirrer, thermocouple, and addition funnel was charged with the product of Example 2C (70 g, 429 mmol) and 48% HBraq (240 mL). The suspension was maintained at 0-5 C. as a solution of NaNO2 (32.0g, 464 mmol) in water (100 mL) was added dropwise over 1 hour. Additional water (200 mL) was added and the mixture was stirred for 10 minutes at 0-5 C. The mixture was treated with CuBr (32.6 g, 227 mmol) in portions over 20 minutes followed by additional water to maintain a fluid reaction mixture. The mixture was allowed to warm to room temperature and diluted with water. The mixture was distilled at ambient pressure, until the distillate ran clear (1.5 L collected). The distillate was extracted with EtOAc (3*500 mL) and the combined extracts were washed with brine (100 mL), dried (MgSO4), and concentrated to provide 5-bromo-2,3-dichloropyridine as a solid. 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, J=3 Hz, 1H), 8.38 (d, J=3 Hz, 1H).

According to the analysis of related databases, 98121-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2004/242644; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1214328-96-7 ,Some common heterocyclic compound, 1214328-96-7, molecular formula is C7H5BrClNO2, 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 the solution of methyl 3-bromo-6-chloropyridine-2-carboxylate (5.0 g, 19.9 mmol) and MeOH (1.0 mL, 25.8 mmol) in THF (15.0 mL, freshly dried over NaH) was added /-BuOK (29.8 mL, 29.8 mmol, 1 M in THF) slowly over 20 min at 0 C under N2 atmosphere. The reaction mixture was stirred at 0 C for 5 min. The reaction mixture was quenched with ice-cold sat. NH4Cl solution (30.0 mL), and extracted with EtOAc (50.0 mL x 2) rapidly. The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by flash silica gel chromatography (40 g column, EtOAc in petroleum ether from 0% ~ 10%) to give methyl-3 -bromo-6-methoxypyridine-2- carboxylate (4.5 g, 92.0% yield) as a colorless oil.

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. 1214328-96-7, Methyl 3-bromo-6-chloropicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63572-73-6 ,Some common heterocyclic compound, 63572-73-6, molecular formula is C6H4N4O2, 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 5-nitro-1H-pyrazolo [4,3-b]pyridine (7.3 g,38.0 mmol) in MeOH (240 mL) was added 10% wt Pd/C (4.03,3.8 mmol). The reaction mixture was hydrogenated underhydrogen (1 atm) for 16 h. The Pd/C was removed by filtration, andthe filtrate was concentrated to give 1H-pyrazolo [4,3-b]pyridin-5-amine (5.1 g, 82% yield) as a light brown solid. Rf: 0.33 (DCM/MeOH,19/1, v/v). Mp: 178 C. 1H NMR (DMSO-d6, 400 MHz) d 13.12 (s, 1H),8.05 (d, J 2.4 Hz, 1H), 7.81 (s, 1H), 7.18 (d, J 2.3 Hz, 1H), 5.04 (s,2H). MS (ESI)m/z:134.8 [MH],156.7 [MNa], 301.0 [2MNa].

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. 63572-73-6, 5-Nitro-1H-pyrazolo[3,4-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hao, Chenzhou; Huang, Wanxu; Li, Xiaodong; Guo, Jing; Chen, Meng; Yan, Zizheng; Wang, Kai; Jiang, Xiaolin; Song, Shuai; Wang, Jian; Zhao, Dongmei; Li, Feng; Cheng, Maosheng; European Journal of Medicinal Chemistry; vol. 131; (2017); p. 1 – 13;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98273-79-1, Methyl 3-chloroisonicotinate, 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: 98273-79-1, blongs to pyridine-derivatives compound. Recommanded Product: 98273-79-1

A 2.5 M hexane solution of BuLi (16.79 mL, 42.0 mmol) was added dropwise to a solution of diisopropylamine (6.23 mL, 43.7 mmol) in THF (150 mL) at -78 0C. The mixture was stirred at 0 0C for 15 min and cooled to -78 0C. Acetonitrile (2.192 mL, 42.0 mmol) was added dropwise. The solution gradually turned to milky white. After 1 h at -78 0C, methyl 3-chloroisonicotinate (3.00 g, 17.48 mmol) in THF (10 mL) was added dropwise. The flask was rinsed with THF (2 mL) and added. After 1 h at -78 0C, the mixture was quenched with brine (200 mL) and acidified to pH~l. THF was evaporated in vacuo. The aqueous residue was extracted withEtOAc (3×100 mL). The combined extracts were washed with brine (50 mL), dried (MgSO4) and concentrated to give impure 3-(3-chloropyridin-4-yl)-3- oxopropanenitrile as a tan solid (3.12 g, 81% pure, 80% yield). MS (ES+) m/z: 181 (M+H); LC retention time: 1.90 min (analytical HPLC Method A).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/100171; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 80537-07-1, 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 80537-07-1 as follows.

2-Phenylpyrazolo[1,5-a]pyridine An o-dichlorobenzene solution (42 mL) of 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid (10.0 g) was stirred at 160C for 2 hours under an argon atmosphere. The reaction solution was evaporated under vacuum and the obtained solid was washed with n-hexane to obtain a title compound as a brown solid (9.45 g). 1H-NMR (400 MHz, CDCl3) delta 6.72 (1H, td, J = 7.3,1.2 Hz), 6.79 (1H, s), 7.05-7.11 (1H, m), 7.18-7.21 (2H, m), 7.34-7.39 (1H, m), 7.44-7.49 (1H, m), 7.97 (2H, d, J = 7.3 Hz), 8.47 (1H, d, J = 7.9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,80537-07-1, its application will become more common.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; Kissei Pharmaceutical Co., Ltd.; SETO, Shigeki; UMEI, Kentaro; NISHIGAYA, Yosuke; TANIOKA, Asao; KONDO, Tatsuhiro; KONDO, Atsushi; TATANI, Kazuya; KAWAMURA, Naohiro; EP2669285; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 147619-40-7, 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 147619-40-7, name is 5-Chloro-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

Add in 250ml three-necked flask5-chloro-4-methoxy-3-cyano-2- (1H) pyridone,48percent hydrobromic acid 150 ml,Heating reflux reaction for about 20-24 hours,Stop the reaction, this time the system is dark red solution.The reaction solution was concentrated at 90-95 ° C under reduced pressure to dryness,Add 200ml purified water beating,After stirring for 1 hour, the filtrate was filtered.Filter cake in 55-60 blast drying,Brown solid,That gimeracil,Weight 6.57 g, yield 83.2percentPurity of 99.91percent (see Figure 1),

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 147619-40-7, 5-Chloro-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile.

Reference:
Patent; Nanjing Zhengda Tianqing Pharmaceutical Co., Ltd.; Zheng, Likang; Guo, Xuan; Zhang, Ping; Zhang, Linlin; Chai, Yuzhu; Xu, Dan; Yang, Zhimin; Tian, Zhoushan; (14 pag.)CN104592102; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135900-33-3, 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. 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, 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.

0383] To a solution of 8-chloroquinoline-7-carboxylic acid Int-56 (Example 166) (0.139 g, 0.674 mmol) in DMF (5 mL) was added DIPEA (0.49 mL 2.808 mmol), followed by HATU (0.42 g, 1.123 mmol) at 0 C, and the reaction mixture was stirred at 0 C for 15 min. Then 6- (trifluoromethoxy)pyridin-3 -amine (0.1 g, 0.561 mmol) was added to reaction mixture at 0 C. The reaction mixture was stirred at r.t. for 16 hrs. After completion of the reaction, the reaction mixture was diluted with water (10 mL) and extracted with Ethyl Acetate (2×50 mL). Combined organic layers were washed with water (2×30 mL), brine (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude product was purified by column chromatography (100-200 silica gel) using 50% Ethyl Acetate in Hexane as eluent to afford 50 mg (24% yield) of 8-chloro-N-(6-(trifluoromethoxy)pyridin-3-yl)quinoline-7-carboxamide 169 as an off-white solid. 1H-NMR (400 MHz, DMSO-d6): delta 11.08 (s, 1H), 9.12 (dd, J = 4.4, 1.6 Hz, 1H), 8.68 (d, J = 2.4 Hz, 1H), 8.55 (J = 8.4, 1.6 Hz, 1H), 8.37 (dd, J = 8.8, 2.4 Hz, 1H), 8.13 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 8.8 Hz, 1H), 7.75 (dd, J= 8.4, 4.0 Hz, 1H), 7.38 (d, J= 8.8 Hz, 1H); MS (ESI) m/z 368.24 [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 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1221171-70-5, 2-Chloro-6-(trifluoromethoxy)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, Formula: C6H3ClF3NO, blongs to pyridine-derivatives compound. Formula: C6H3ClF3NO

[00532] An LDA solution was prepared from n-BuLi (2.5M in hexane, 9.0 mL, 22.4mmols, 1.3 eq) and diisopropylamine (2.60 g, 25.9 mmols, 1.5 eq) in THF (10 mL) at 0C. To the LDA solution was added a solution of 77 (3.40 g, 17.3 mmols, 1.0 eq) in THF(10 mL) dropwise at -78 C. The solution was stirred at -78 C for 2 hours. After TMSC1 (2.42 g, 22.4 mmols, 1.3 eq) was added dropwise, the reaction mixture was allowed to warm up to room temperature and stirred for 1 hour. Water (120 mL) was added. The aqueous layer was extracted with ethyl acetate (100 mL x 3), and the combined organic layers were dried over Na2SO4 and concentrated. The crude was purified on silica gel using petroleum ether (100 percent) as an eluent to afford the desired compound 78 (3.90 g, 14.4 mmols, 83.2%) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1221171-70-5, 2-Chloro-6-(trifluoromethoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ALPHARMAGEN, LLC; PUTMAN, David, G.; DASSE, Olivier; HOGENKAMP, Derk; (154 pag.)WO2016/144792; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 127446-34-8, 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. 127446-34-8, name is N-(6-Chloro-3-formylpyridin-2-yl)pivalamide. A new synthetic method of this compound is introduced below.

To a solution of Lambda/-(6-chloro-3-formylpyridin-2-yl)pivalamide (prepared as described in J. Org. Chem. (1990), 55, 4744; 3.0 g, 12.64 mmol) in MeCN (250 niL) was added triethyl 2-fluoro-phosphonoacetate (4 g, 16.51 mmol), lithium chloride (0.935 g) and DBU (2.8 mL, 18.7 mmol). The mixture was stirred at rt for 4 h. The solvent was evaporated and the residue was partitioned between N HCl (100 mL) and ether (150 mL). The aq. layer was extracted with ether (10O mL) and the combined ethereal layers were dried over Na2SO4, filtered and concentrated to dryness. The residue was taken up in dioxane (15 mL) and 6JV EtaC1 (50 mL) was added. The mixture was heated to reflux for 90 min. The mixture was cooled to 00C and the volatiles were removed in vacuo. The solids were filtered off and washed with water. The solid was dried in vacuo to afford the title compound as a yellow solid (1.38 g, 56% yield). The title compound was only 70% pure. MS (ESI, m/z): 199.1 [M+Eta+] for C8H4N2OClF.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,127446-34-8, N-(6-Chloro-3-formylpyridin-2-yl)pivalamide, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/116337; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem