Pyridine-derivatives

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.106877-33-2, name is 5-Amino-2-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.name: 5-Amino-2-(trifluoromethyl)pyridine

EXAMPLE 3 [0186] [CHEMMOL-00538] [0187] Step 1 [0188] 3-Amino-6(trifluoromethyl)pyridine (1.0 g, 6.2 mmol), N-Boc-4-piperidone (1.5 g, 7.4 mmol), Na(AcO)3BH (2.0 g, 9.3 mmol), and AcOH (0.35 mL, 6.2 mmol) were taken up in 1,2-dichloroethane and stirred at 55 C. for 17 hours. The solution was diluted with CH2Cl2 and quenched with 1 N NaOH. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated to furnish a yellow oil. The residue was resubjected to the reaction conditions for 20 hours. After workup, a yellow oil was obtained. The amine product was purified via recrystallization (CH2Cl2/hexanes) to give 1.6 g (75%) of the amine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,106877-33-2, 5-Amino-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US2004/10008; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63071-03-4 ,Some common heterocyclic compound, 63071-03-4, molecular formula is C7H9NO, 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 A: methyl 2-(6-methoxypyridin-2-yl)acetate To the solution of LDA (18.3 mL, 36.5 mmol) in THF (120 mL) cooled to -78 C. was added 2-methoxy-6-methylpyridine (1.5 g, 12.2 mmol) in THF (15 mL) dropwise, and then the mixture was stirred at -78 degree for 2 h. Dimethyl carbonate (1.2 mL, 14.6 mmol) was added quickly and continued to stir at -78 C. for 15 min. The reaction was quenched by H2O at -78 C. The solution was extracted with ethyl acetate, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified with a standard method to give desired compound. _?H NMR (CHEOROFORM-d) oe: 7.55 (dd, J8.3,7.3 Hz, 1H), 6.85 (d, J7.3 Hz, 1H), 6.65 (d, J8.3 Hz, 1H),3.92 (s, 3H), 3.77 (s, 2H), 3.74 (s, 3H). EC-MS: mlz (M+H)182.6.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63071-03-4, its application will become more common.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC; Lemieux, Rene M.; Popovici-Muller, Janeta; Salituro, Francesco G.; Saunders, Jeffrey O.; Travins, Jeremy; Chen, Yongsheng; US2014/142081; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1083181-26-3 , The common heterocyclic compound, 1083181-26-3, name is 3-Iodo-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5IN2, 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.

Sodium hydride (140 mg, 60% dispersion in mineral oil) was added to a solution of 3-iodo-1H-pyrrolo[3,2-b]pyridine (Intermediate 1), (700 mg) in dimethyl acetamide (7 mL) at 0 C. The RM was allowed to warm to rt and was stirred for 30 min. To which, was added 4-fluoro-4′-methyl-1,1′-biphenyl (Intermediate 71), (840 mg) and the reaction mixture stirred for a further 1 h. The reaction was quenched with water (20 mL) and extracted with EtOAc (3*20 mL). The organic phases were combined, dried (Na2SO4), filtered, and evaporated under vacuum. The crude product was purified by column chromatography (silica), eluting with 20:80 EtOAc/hexanes to afford the title compound (700 mg). LCMS: m/z 429.04 [M+H]+. 1H NMR (400 MHz, DMSO-d6) ppm 5.51 (s, 2H), 7.21 (dd, J=8.2, 4.6 Hz, 1H), 7.23-7.30 (m, 2H), 7.35 (d, J=8.2 Hz, 2H), 7.54-7.62 (m, 2H), 7.62-7.69 (m, 2H), 8.00 (dd, J=8.2, 1.2 Hz, 1H), 8.09 (s, 1H), 8.40 (dd, J=4.4, 1.4 Hz, 1H)

The synthetic route of 1083181-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); A1;,
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.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.Computed Properties of C5H5ClN2

Intermediate 252A: 2-chloro-5-iodopyridin-4-amine To a stirred solution of 2-chloropyridin-4-amine (5 g, 39 mmol) in DMF (50 mL) was added NIS (8.75 g, 39 mmol). The reaction mixture was then heated at 80 C for 3 h. The mixture was cooled and the DMF removed in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The organic layer was dried over Na2S04, filtered, and concentrated. The product was purified via column chromatography (10% EtO Ac/pet ether) to afford 2-chloro-5-iodopyridin-4-amine (4 g, 39% yield). LCMS: 254.8 (M+). Further elution with 12% EtO Ac/pet ether afforded 2- chloro-3-iodopyridin-4-amine (4 g, 39% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14432-12-3, 4-Amino-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100367-39-3, Adding some certain compound to certain chemical reactions, such as: 100367-39-3, name is 4-Bromo-2-methoxypyridine,molecular formula is C6H6BrNO, 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 100367-39-3.

To a resealable reaction pressure vessel under nitrogen wasadded 1.0 equiv of 9 (266 mg, 0.665 mmol), Pd(PPh3)4 (38 mg,0.033 mmol, 5 mol %), K2CO3 (184 mg, 1.33 mmol, 2.0 equiv), 2-methoxy-4-bromopyridine (137 mg, 0.732 mmol, 1.1 equiv),dioxane (20 mL) and water (2 mL). The mixture was degassedthrough bubbling nitrogen for 40 min and heated at 110 C overnight.After cooling to room temperature, water (20 mL) wasadded and the organic product was extracted using EtOAc(3 30 mL). The combined organic layers were dried overMgSO4, filtered through Celite and the solvent removed in vacuo.The residual was purified on a silica gel column eluted withEtOAc/hexanes to provide 160 mg (63%) of 8e as a colorless oil.

According to the analysis of related databases, 100367-39-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ondachi, Pauline W.; Ye, Zhuo; Castro, Ana H.; Luetje, Charles W.; Damaj, M. Imad; Mascarella, S. Wayne; Navarro, Hernan A.; Carroll, F. Ivy; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5693 – 5701;,
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.1211537-08-4, name is 4,5-Difluoropyridin-2-amine, molecular formula is C5H4F2N2, molecular weight is 130.1, as common compound, the synthetic route is as follows.SDS of cas: 1211537-08-4

36 · 8 g (0 · 28 mol) of 2-amino-4,5-difluoropyridine, 40 · 57 g (0 · 23 mol) of D-glucopyranose and acetonitrile with 10% hydrochloric acid solution (volume ratio 1: 1) A mixture of 200 ml was added to a 500 ml round bottom flask, heated to reflux for 30 minutes, naturally cooled to room temperature, suction filtered, recrystallized from a mixture of acetonitrile:ethanol = 2:1, dried at 60 C vacuum. 10 hours, get 61.15 grams of white solid product, the yield is 90.97%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211537-08-4, 4,5-Difluoropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Henan Chemical Institute Co., Ltd.; Huo Erfu; Cheng Weiqin; Feng Ming; Wang Bonan; Wang Yanhua; Yang Shuai; Wang Yinan; Yang Xianhong; Wang Fang; Han Juan; Zhang Qianhua; Liu Xiuwei; Gao Qinghuan; (17 pag.)CN109824742; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 114077-82-6, 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 114077-82-6, name is 4-Chloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Example 5 4-chloro-3-hydroxymethylpyridine To a solution of 4-chloro-3-pyridyl carboxyaldehyde (140 mg, 1.0 mmol) in THF (1 mL) at 0° C. was added methanol (1 mL) followed by portionwise addition of sodium borohydride (75 mg, 2.0 mmol). After 1 hr, acetic acid (0.15 ml) was added and the reaction mixture was evaporated to dryness with rotary evaporator at room temperature. The solid residue was chromatographed on silica gel column (1percent MeOH/dichloromethane) to afford 60 mg (42percent) of the title compound. 1H NMR (CDCl3) delta 4.30 (br s, 1H), 4.80 (s, 2H), 7.30 (d, 1H, J=5), 8.34 (d, 1H, J=5), 8.62 (s, 1H).

According to the analysis of related databases, 114077-82-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Microcide Pharmaceuticals, Inc.; US6066630; (2000); A;; ; Patent; Microcide Pharmaceuticals, Inc.; US6087355; (2000); A;; ; Patent; Microcide Pharmaceuticals, Inc.; US5859256; (1999); A;,
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 945717-09-9, name is 2-Chloro-4-ethynylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloro-4-ethynylpyridine

To a solution of the compound i18 (1g, 1.95mmol) in DMF (10mL) was added Et3 N (0.812mL, 5.86mmol), 2-chloro-4-ethynylpyridine (806mg, 5.86mmol), copper iodide (37.2mg, 0.195mmol), and PdCl2 (PPh3)2(137mg,0.195mmol), the mixture was stirred under nitrogen atomosphere at 100 C for 1 hour. Water was added to the reactionsolution, extracted with ethyl acetate, and the organic layer was washed water, dried over anhydrous sodium sulfate,concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane – ethylacetate) to yield the compound 23 (574mg, yield 56%). LC/MS (ESI):m/z = 522.20 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 945717-09-9.

Reference:
Patent; Shionogi & Co., Ltd.; KAWASUJI, Takashi; TANIYAMA, Daisuke; SUGIYAMA, Shuichi; TAMURA, Yoshinori; (153 pag.)EP3144311; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 633328-33-3, name is 3-Bromo-1H-pyrazolo[4,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Bromo-1H-pyrazolo[4,3-b]pyridine

To a solution of 3-bromo-1H-pyrazolo[4,3-b]pyridine (1.0 eq., 100 mg, 0.505 mmol) in 1-methyl-2-pyrrolidinone (1.3 mL) in a microwave vial was added copper(I) cyanide (1.5 eq., 69.2 mg, 0.757 mmol). The reaction was heated in the microwave to 220 C for 20 minutes. Thesolution was then cooled to room temperature, diluted with aqueous saturated ammonium chloride and extracted twice with DCM. The organic layers were combined, dried with sodium sulfate and concentrated. The crude material was purified by flash chromatography (5 – 100% iPrOAc in heptanes) to afford 70 mg (96 %) of the desired product with minor impurities.

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, 633328-33-3, 3-Bromo-1H-pyrazolo[4,3-b]pyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 159503-91-0, 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 159503-91-0, name is tert-Butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

2nd step: under the protection of nitrogen, the 1M isopropyl magnesium chloride-lithium chloride (88 ml, 88mmol) into the reaction bottle, temperature control -15 C to -5 C, dropwise N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo, 2-methyl tetrahydrofuran (90 ml) solution, stirring finishing joining 1-2 hours. After the end of the exchange, then drop by adding isopropoxy boric acid pinacone ester (16.4g, 88mmol), subsequently maintain the reaction at room temperature overnight. Adding 10% hydrochloric acid aqueous solution quenching reaction, adjusting PH= 4-5, by adding 160 ml ethyl acetate, saturated salt water an organic layer, the organic layer after evaporation to dryness, add ethanol/heptane 5:1 obtained after pulping 18.9g N-Boc-1 needle-like white crystals, 2, 5, 6-tetrahydro-pyridine-4-boronic acid frequency that alcohol ester, GC: 99.6%, yield: 61%.

According to the analysis of related databases, 159503-91-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cangzhou Purui Oriental Technology Co., Ltd; Leng, Yanguo; Zhang, Shihong; Liu, Jinzou; (6 pag.)CN105566367; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem