Tag: M.W:200-300

Synthetic Route of 1156542-28-7 , The common heterocyclic compound, 1156542-28-7, name is 5-Chloro-4-(trifluoromethyl)picolinonitrile, molecular formula is C7H2ClF3N2, 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 7 ml of ethanol were added 0.61 g of sodium bicarbonate and 0.5 g of hydroxylamine hydrochloride, and the mixture was heated to reflux for 1 hour. After allowing to cool, 0.74 g of 5-chloro-4-trifluoromethylpyridine-2-carbonitrile was added at O0C, and the mixture was stirred for 5 hours, and concentrated. To the residue was added water, the resultant solution was extracted with ethyl acetate three times, and the organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.6 g of 5-chloro-4- trifluoromethylpyridine-2-carboxamide=oxime. 5-Chloro-4-trifluoromethylpyridine-2-carboxamide=oxime1H-NMR (DMSO-d6): 6.02 (s, 2H), 8.14 (s, IH), 8.93 (s, IH), 10.31 (s, IH)

The synthetic route of 1156542-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/66786; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 863704-60-3, 6-(4-Fluorophenyl)picolinic acid, 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, Quality Control of 6-(4-Fluorophenyl)picolinic acid, blongs to pyridine-derivatives compound. Quality Control of 6-(4-Fluorophenyl)picolinic acid

A mixture of picolinic acid derivative (1.0 g, 4.6 mmol), Na2HPO4 (1.2 g) and m-CPBA (1.1 g, 70% from Aldrich) in CH2ClCH2Cl (30 mL) was stirred at rt for 2 h. Additional Na2HPO4 (0.8 g) and m-CPBA (1.0 g) was added to the reaction mixture and it was stirred for 3 h at rt. Another Na2HPO4 (0.5 g) and m-CPBA (0.5 g) was added to the reaction mixture and it was stirred at rt overnight. CHCl3 (160 mL) and 2 N aq. HCl solution (50 mL) were added to the reation mixture and the organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with EtOAc/MeOH/HOAc//700:240:60 to obtain the desired product which was contaminated with m-CPBA. This impure material was purified by preparative HPLC to obtain the desired product (175 mg, 16%) as a white solid. 1H NMR (DMF-d7) 8.45 (dd, 1H, J=8.3, 2.2 Hz), 8.15 (d, 1H, J=2.2 Hz), 8.13-8.00 (m, 4H), 7.45 (t, 2H, J=8.7 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,863704-60-3, 6-(4-Fluorophenyl)picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Borzilleri, Robert M.; Cornelius, Lyndon A.M.; Schmidt, Robert J.; Schroeder, Gretchen M.; Kim, Kyoung S.; US2005/245530; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 78760-60-8 ,Some common heterocyclic compound, 78760-60-8, molecular formula is C13H10N2O, 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.

Step D: at -5 ~ 0 , a 2M ethylmagnesium bromide in THF (26.5mL, 53mmol) was added dropwise to compound 25 (8.6g, 40.9mmol) in THF (30 mL) solution. After the addition was completed, the resulting mixture was further stirred at this temperature for 1 hour. Slowly add water (90mL),Adjust the pH to 3~4 with 2M hydrochloric acid.Extracted with ethyl acetate (100 mL × 3),The combined organic phases were washed with water (50 mL) and brine brineThe solvent was evaporated under reduced pressure to give 1-(5-benzyloxypyridin-2-yl)propan-1-one (26) (9.74 g). The yield was 98.7%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78760-60-8, its application will become more common.

Reference:
Patent; Jiangsu Xin Element Pharmaceutical Technology Co., Ltd.; Shi Dongfang; Fu Changjin; Cheng Xi; Gong Weiwei; Gu Jie; Li Pengfei; Zhang Min; Yang Yan; Jin Wenqing; (51 pag.)CN110183431; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 670253-37-9, 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 670253-37-9, name is 4-Chloro-5-iodopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-chloro-5-iodo-pyridin-2-ylamine (64.2 g, 0.25 mol) in methanol (1.1 L) and TFA (93.7 mL, 1.26 mol) was added tert-butyl nitrite (150 mL, 1.26 mol) so as to maintain temperature less than 3 C. The resultant mixture was stirred at RT for 1 h then allowed to warm to RT and stirred for 16 h. The reaction was quenched by the careful addition of water then concentrated in vacuo to one-fourth of the volume. The resultant residue was treated with water (1 L) and the precipitate formed collected by filtration and dried in vacuo at 35 C. to give the title compound (62.3 g, 92%). Contains 16% impurity. 1H NMR 400 MHz (DMSO-d6) delta: 8.56 (1H, s), 7.20 (1H, s), 3.86 (3H, s).

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 670253-37-9, 4-Chloro-5-iodopyridin-2-amine.

Reference:
Patent; Genentech, Inc.; US2012/245144; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84199-61-1, 3-Acetyl-2-bromopyridine, 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, COA of Formula: C7H6BrNO, blongs to pyridine-derivatives compound. COA of Formula: C7H6BrNO

General procedure: An solution of indicated quantity of DAST in dry CH2Cl2 was added dropwise to a solution of 14 (26.9mmol) in dry CH2Cl2 (50mL) at 0C. The reaction mixture was warmed to rt and stirred for indicated period of time. The resulting mixture was poured into H2O (50mL), sat. aq NaHCO3 was added to pH=8, and organic phase was separated. The aqueous layer was extracted with CH2Cl2 (3×50mL), the combined organic layers were dried over Na2SO4, and then evaporated under reduced pressure.

The synthetic route of 84199-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Subota, Andrii I.; Ryabukhin, Sergey V.; Gorlova, Alina O.; Grygorenko, Oleksandr O.; Volochnyuk, Dmitriy M.; Journal of Fluorine Chemistry; vol. 224; (2019); p. 61 – 66;,
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. 914358-72-8, name is 5-Bromo-3-chloro-2-methylpyridine, molecular formula is C6H5BrClN, 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. Safety of 5-Bromo-3-chloro-2-methylpyridine

A mixture of tert-butyl 2-(3-acetyl-5-(4, 4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)acetate (S2, 100 mg, 1 equiv), 5-bromo-3-chloro-2-methylpyridine (S3, 62 mg, 1.2 equiv), and cesium carbonate (230 mg, 2.8 equiv) in DMF (8 mL) was purged with argon for 5 min. 1,1?-Bis(diphenylphosphino)ferrocenedichloropalladium(II) (14 mg, 0.06 equiv) was then added under argon and the reaction mixture w is heated to 90 C. overnight. The reaction mixture was cooled to room temperature and diluted with EtOAc (20 mL) and water (10 ml). The organic layer was then separated, washed with brine (3×15 mL), dried, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (5% MeOH in DCM) to give 100 mg of tert-butyl 2-(3-acetyl-5-(5-chloro-6-methylpyridin-3-yl)-1H-indol-1-yl)acetate (S4) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 914358-72-8.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 880870-13-3, 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 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

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.

According to the analysis of related databases, 880870-13-3, the application of this compound in the production field has become more and more popular.

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

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. 42521-09-5, name is Methyl 2,6-dichloroisonicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2,6-dichloroisonicotinate

Under inert atmosphere, a mixture of methyl 2,6-dichloropyridine-4-carboxylate (2,00 g), dimethylzinc (2N in toluene, 14.6 ml, 3.0 equiv.) and PdCI2(dppf)2 (400 mg, 0.05 equiv.) in dioxane (50 ml), was heated at 80C for 4Hrs. The reaction mixture was cooled by an ice bath, hydrolysed with water (100 ml) and filtered through a pad of celite. The pad was rinsed with water and EtAOc. The filtrate was extracted with EtOAc (250 ml). The organic layer was washed with brine (1 00 ml), dried over MgSO4 and concentrated. Purification by flash chromatography (MeOH in CH2Cl2, 0 to 2%) afforded compound 99 as an orange oil in 96% yield. 1H-NMR (400 MHz, DMSO): 2.51 (s, 6H, 2CH3); 3.88 (s, 3H, O-CH3); 7.51 (s, 2H, Ar). M/Z(M+H)+ = 166.1.

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, 42521-09-5, Methyl 2,6-dichloroisonicotinate.

Reference:
Patent; DOMAIN THERAPEUTICS; MAYER, Stanislas; SCHANN, Stephan; WO2013/174822; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 185017-72-5, 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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-2-chloro-6-methylpyridine (47.8 mg, 0.231 mmol) and 2- (cyclopentylmethyl) oxazole (35 mg, 0.231 mmol) in DMA (1 mL) was added potassium acetate (45.4 mg, 0.463 mmol) and Pd (PPh3)4(26.7 mg, 0.023 mmol) under N2. The reaction mixture was stirred at 90 overnight. The reaction mixture was cooled to room temperature, filtered and the filtration was concentrated in vacuum, the residue was purified by Prep. TLC (PE: EA 10: 1) to give the title compound. MS: 277.1 (M+1) .1H NMR (CDCl3-d, 400 MHz) : delta 7.95 (d, J 7.8 Hz, 1H) , 7.66 (bs, 1H) , 7.16 (d, J 7.8 Hz, 1H) , 2.82 (d, J 7.0 Hz, 2H) , 2.31-2.39 (m, 1H) , 1.83 (bs, 4H) , 1.65 (bs, 2H) , 1.27 (d, J 5.5 Hz, 2H) .

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 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; BAO, Jianming; HENDERSON, Timothy J.; LO, Michael Man-chu; MAZZOLA, JR., Robert D.; RUDD, Michael T.; TELLERS, David M.; TONG, Ling; LI, Chunsing; NA, Meng; (144 pag.)WO2019/238; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 799293-73-5, Adding some certain compound to certain chemical reactions, such as: 799293-73-5, name is 3-Bromofuro[3,2-c]pyridin-4-amine,molecular formula is C7H5BrN2O, 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 799293-73-5.

1, 1-dimet ylet yl 5-(4-aminofuro[3,2-clDyridin-3-yl)-2,3-di vdro-1H-indole-1-carboxylate 3-Bromofuro[3,2-c]pyridin-4-amine (7.23 g, 33.9 mmol), 1 , 1-dimethylethyl 5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-indole-1-carboxylate (12.90 g, 37.4 mmol), PdCI2(dppf)-CH2CI2 adduct (1 .39 g, 1 .702 mmol), 1 ,4-Dioxane (300 mL), and saturated aqueous sodium bicarbonate (100 mL, 100 mmol) were added to a 3-neck, 1 L flask equipped with a reflux condenser and a heating mantle. The flask was evacuated and filled with nitrogen 4 times, and then the mixture was stirred at reflux under Nitrogen for 2 hr. HPLC showed complete conversion, so it was cooled and allowed to stir at room temperature overnight. The crude mixture was then filtered through celite, rinsing with EtOAc (500 mL). The filtrate was washed with half-saturated aqueous NaHC03 (500 mL), and the aqueous phase was back-extracted with ethyl acetate (1 * 500 mL). The combined organic phases was washed with brine (1 * 500 mL), dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (Analogix, 600 g Si02, 20%-100% EtOAc in hexanes gradient over 60 minutes, then 100% EtOAc for 30 more minutes). The product fractions were combined and concentrated in vacuo to give 1 , 1-dimethylethyl 5-(4-aminofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1 H-indole-1 – carboxylate (9.23 g, 26.3 mmol, 77 % yield) as an off-white solid. LC/MS (ES) m/z = 352 [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. 799293-73-5, 3-Bromofuro[3,2-c]pyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem