Day: March 15, 2021

Electric Literature of 1480-65-5 ,Some common heterocyclic compound, 1480-65-5, molecular formula is C5H3ClFN, 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-chloro-2-fluoropyridine (500 mg, 3.80 mmol), DIEA (1.5 g, 11.61 mmol), methyl 2-(piperidin-4-yl)acetate (599 mg, 3.81 mmol) in DMSO (10 mL) was stirred for 16 h at 90 ¡ãC under N2. The resulting solution was extracted with 2×50 mL of EtOAc, and the combined organic layers were concentrated under vacuum and purified with silica gel chromatography using EtOAc / hexane (1/1) to afford 700 mg (69percent) of the title compound as an off-white solid. -MS (ES, m/z): 268.9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1480-65-5, its application will become more common.

Reference:
Patent; CENTAURUS THERAPEUTICS; ROMERO, Donna L.; MCCALL, John M.; BLITZER, Jeremy; (118 pag.)WO2018/112077; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1628-89-3, 2-Methoxypyridine, 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, 1628-89-3, blongs to pyridine-derivatives compound. COA of Formula: C6H7NO

A solution of 2-methoxy-pyridine (100 g, 0.92 mole), NBS (180 g, 1.0 mole) inacetonitrile (1. OL) was stirred at reflux for 21 h. TLC showed that the reaction wascomplete. The reaction mixture was cooled to room temperature and concentrated. 900ml solvent was collected. The resulting suspension was filtered and washed with n-hexane (400mL). The filtrate was concentrated again to afford crude product. The cmde product was distilled at reduced pressure (30C[-0.3mmHg) to afford the title compound as a clearoil (146 g, 84%). LCMS (m/z): 190.0 [M+1f ?H NMR (400 MHz, CDC13): oe 3.90 (s,3H), 6.65 (d, J= 8.8 Hz, 1H), 7.62 (dd, J= 8.8 Hz, 2.4Hz, 1H), 8.19 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1628-89-3, its application will become more common.

Reference:
Patent; CURIS, INC.; FATTAEY, Ali; RHYASEN, Garrett, W.; (61 pag.)WO2018/85342; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18437-58-6, 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.18437-58-6, name is 4-Amino-2-picoline, molecular formula is C6H8N2, molecular weight is 108.14, as common compound, the synthetic route is as follows.

General procedure: To a solution of substituted acetylsalicyloyl chlorides (0.022 mol) in anhydrous chloroform (100 mL) was added triethylamine (0.023 mol) at 4 C. After the mixture was stirred for 5-15 min and then substituted 4-amino pyridinewas added portion wise in the ice bath. After warmed to room temperature, the solution was stirred for 24-48 h and then quenched by 1 mL of 1 M hydrochloric acid. The reaction mixture was extracted with 10 % hydrochloric acid (50, 30and 30 mL) and the combined aqueous was basified to pH 7-9 with cooled saturated sodium bicarbonate solution. The yellow precipitation was filtered producing the crude products. After recrystallized in ethanol, the products were isolated as pure form in more than 85 % yields.

Statistics shows that 18437-58-6 is playing an increasingly important role. we look forward to future research findings about 4-Amino-2-picoline.

Reference:
Article; Dian, He; Zhou, De-Bin; Mou, Jian-Ping; Yang, Zhu-Qing; Zhong, Jia; Ding, Xiao-Quan; Li, Chong; Wang, Xiao-Hong; Zhang, Jian-Gang; Asian Journal of Chemistry; vol. 26; 21; (2014); p. 7269 – 7275;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58596-89-7, 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.58596-89-7, name is 2,6-Dichloro-5-methylpyridin-3-amine, molecular formula is C6H6Cl2N2, molecular weight is 177.0312, as common compound, the synthetic route is as follows.

EXAMPLE A 2,6-Dichloro-3-methyl-5-(3,3-dimethyl-1-triazeno)-pyridine STR15 285 ml of half-concentrated hydrochloric acid are slowly added to 43 g (0.24 mole) of 5-amino-2,6-dichloro-3-methyl-pyridine (Helv. Chim. Acta 59, 190 [1976]), the mixture is cooled to 0, a solution of 17.2 g (0.25 mole) of sodium nitrite in 70 ml of water is added dropwise and the mixture is subsequently stirred at 0 for some time. This diazonium salt solution is added dropwise to a solution of 150 g of sodium carbonate in 430 ml of water and 70 ml of 40-50% strength aqueous dimethylamine solution at 0-3 in the course of 90 minutes and the mixture is subsequently stirred at 0. The precipitate is filtered off with suction, rinsed thoroughly with water and dried under a high vacuum at 40 C. Yield: 49.3 g (88% of theory), melting point: 91-95 C.

Statistics shows that 58596-89-7 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloro-5-methylpyridin-3-amine.

Reference:
Patent; Bayer Aktiengesellschaft; US4840954; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 10386-27-3 , The common heterocyclic compound, 10386-27-3, name is 2-Bromoisonicotinonitrile, molecular formula is C6H3BrN2, 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 25 mL-flask were addedethyl 2-((45)-4-((1-(2-chlorophenyl)-2-(3,3- difluorocyclobutylamino)-2-oxoethyl) (3 -fluoro -phenyl)carbamoyl)-2-oxoimidazolidin- 1- yl)acetate (50 mg, 0.0882 mmol), 2-bromoisonicotinonitrile (21 mg, 0.115 mmol), Cs2CO3 (58 mg,0.176 mmol), Xant-Phos (5.2 mg, 0.OO9mmol), Pd2(dba)3 (8.2 mg, 0.009 mmol) and 1,4- dioxane (1 mL). The mixture was degassed and refilled with nitrogen, and then heated to 100¡ãC for 3hr. The resulting mixture was cooled and filtered and then the filtrate was concentrated in vacuo. The residue was purified by a standard method to give both epimers.?H NMR (400 MFTz, CDC13): 8.63-8.57 (5, 1H), 8.55 ? 8.38 (m, 1H), 7.63 (s, 1H), 7.46 ? 6.84 (m, 8H), 6.45-6.37 (m, 1H), 6.22 ? 5.94 (m,1H), 5.06 ? 4.77 (m, 1H), 4.43-4.37 (m, 1H), 4.32-4.20 (m, 1H), 4.21 (q, J = 7.1 Hz, 2H), 3.82 ? 3.46 (m, 3H), 3.12 ? 2.82 (m, 2H), 2.66 ? 2.25 (m, 2H), 1.29 (t, J = 7.1 Hz, 3H). MS : 669(M+1).

The synthetic route of 10386-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10626; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 74420-15-8, 3-Bromo-1H-pyrrolo[2,3-b]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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

General procedure: In a dry and argon flushed 10 mL Schlenk tube, equipped with a magnetic stirring bar and a septum, Pd(O2CCF3)2 (7 mg, 2 mol%) was dissolvedin anhydrous THF (1 mL). Then, SPhos (16 mg, 4 mol%) was added and the reaction mixture was stirred at r.t. for 10 min, beforethe 3-bromo-7-azaindole (9a; 158 mg, 0.8 mmol, 1.0 equiv) and the previously zincated ester derivative 6 (1.3 mmol, 1.6 equiv) were added subsequently. The mixture was stirred at 50 C for the indicated time. The completion of the reaction was checked by GC analysis of reaction aliquots quenched with H2O (0.5 mL). The mixture was then quenched with a sat. aq NH4Cl (3 mL) and extracted with EtOAc(3 ¡Á 10 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude products 4a and 4b were purifiedby flash chromatography

The synthetic route of 74420-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Barl, Nadja M.; Malakhov, Vladimir; Mathes, Christian; Lustenberger, Philipp; Knochel, Paul; Synthesis; vol. 47; 5; (2015); p. 692 – 700;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.3796-23-4, name is 3-(Trifluoromethyl)pyridine, molecular formula is C6H4F3N, molecular weight is 147.1, as common compound, the synthetic route is as follows.HPLC of Formula: C6H4F3N

General procedure: Add 3-trifluoromethylpyridine (73.6g, 0.5mol) and WCl6 (9.9g, 0.025mol) to a 250mL three-necked flask, purge nitrogen into the flask, heat with stirring to 120 C, and wait for the temperature to stabilize after nitrogen Switch to chlorine gas (100 mL / min), and react for 15 hours at 120 C with chlorine gas bubbling, stop heating, and switch the chlorine gas to nitrogen again to end the reaction.The temperature was then raised to 200 C and the entire product was distilled off. A 10 wt% NaOH solution was added to the steamed product to neutralize it, and extraction and liquid separation were performed to obtain an oily product.The obtained oily product was dried with anhydrous sodium sulfate and weighed 96.0 g.Qualitative analysis was performed by GC-MS, and quantitative analysis was performed by internal standard method of gas chromatography.The results are shown in Table 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3796-23-4, 3-(Trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang Chemical Institute Co., Ltd.; Zhejiang Lantian Environmental Protection Gao Technology Co., Ltd.; Sinochem Lantian Group Co., Ltd.; Yan Bo; Yu Wanjin; Lin Shengda; Liu Minyang; Liu Wucan; Zhang Jianjun; (10 pag.)CN110627711; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.

General procedure: To a stirred degassed mixture of 8a (502 mg, 2.0 mmol), 4a (470 mg, 2.0 mmol), and K2CO3 (552 mg, 4.0 mmol) in dioxane (15 mL) were added CuI (76 mg, 0.4 mmol) and trans-N,N’-dimethyl-cyclohexane-1,2-diamine (56 mg, 0.4 mmol). The reaction vessel was sealed and heated at 110 C for 16 h. The reaction mixture was cooled to rt and concentrated. The resulting residue was diluted with DCM (250 mL), washed with brine (100 mL), dried over Na2SO4, and concentrated. The residue was purified by column chromatography (silica gel, DCM/MeOH = 97/3 to 96/4) to give the title compound (150 mg, 18%) 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. 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Igawa, Hideyuki; Takahashi, Masashi; Shirasaki, Mikio; Kakegawa, Keiko; Kina, Asato; Ikoma, Minoru; Aida, Jumpei; Yasuma, Tsuneo; Okuda, Shoki; Kawata, Yayoi; Noguchi, Toshihiro; Yamamoto, Syunsuke; Fujioka, Yasushi; Kundu, Mrinalkanti; Khamrai, Uttam; Nakayama, Masaharu; Nagisa, Yasutaka; Kasai, Shizuo; Maekawa, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 24; 11; (2016); p. 2486 – 2503;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 82257-15-6, 4-Methoxypyridine-3-carboxaldehyde, 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, name: 4-Methoxypyridine-3-carboxaldehyde, blongs to pyridine-derivatives compound. name: 4-Methoxypyridine-3-carboxaldehyde

{l-[4-(5-Amino-2-phenyl-pyrimidin-4-ylamino)-phenyl]-cyclobutyl}- carbamic acid tert-butyl ester (0.25 g, 0.58 mmol) was dissolved in acetic acid (30 mL), then 4- methoxy-pyridine-3-carbaldehyde (87.7 mg, 0.64 mmol) and Cu(OAc)2 (105 mg, 0.58 mmol) were added separately. The reaction mixture was stirred at 100 C for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (150 mL). The organic layer was washed with aqueous sat. NaHC03 solution, followed by brine, dried over sodium sulfate, filtered and concentrated to give crude desired product (-150 mg), which was used directly without further purification. LC/MS (ESI+): e/z: 549.2 [M+l]+.

The synthetic route of 82257-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19621-92-2, Adding some certain compound to certain chemical reactions, such as: 19621-92-2, name is 6-Oxo-1,6-dihydropyridine-2-carboxylic acid,molecular formula is C6H5NO3, 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 19621-92-2.

Ethyl iodide (112.2 g, 720 mmol, 4 equiv) was added to a suspension of 6-hydroxy – pyridme-2-carboxylic acid (25.0 g, 180 mmol, 1 equiv) and silver(I) carbonate (100 g, 360 mmol, 2 equiv) in CHCb (400 mL). The mixture was stirred at 30C for 1 day. Insoluble material was removed by filtration and the solid was washed with CHCb. The filtrate was concentrated in vacuo to afford the title compound ethyl 6-ethoxypicolinate as light yellow oil which was used in the next step without further purification. LC-MS: m/z 196.0 (M+H) +

According to the analysis of related databases, 19621-92-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANNAPURNA BIO, INC.; TANG, Haifeng; HANSON, Michael; BOYCE, Sarah; NIE, Zhe; (461 pag.)WO2020/73011; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem