Day: September 28, 2021

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

Synthetic Route of 6188-23-4 , The common heterocyclic compound, 6188-23-4, name is 6-Bromoimidazo[1,2-a]pyridine, molecular formula is C7H5BrN2, 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 stirred solution of 38A (1.0 g, 5.08 mmol) in THF (60 mL) under argoncondition was added NaH (0.122 g, 5.08 mmol, 60 % in mineral oil). The reactionmixture was stirred at RT for 30 mm. and to it was added Selectfluor (3.87 g, 10.92 mmol) in acetonitrile (10 mL). The reaction mixture was heated at 70 C for another 20 h. The reaction mixture was quenched with saturated aq. NH4C1 solution (100 mL) and was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried overanhydrous sodium sulfate, filtered and the filtrate evaporated under reduced pressure to get a brown gum. The crude product was purified by silica gel chromatography (24 g RediSep column, eluting with a gradient of 17-19 % EtOAc in petroleum ether). Fractions containing the desired product were combined and evaporated under reduced pressure to afford intermediate 38B (0.1 g, 9.16 % yield). LCMS: m/z = 215.3 [M+HjHPLC Ret. Time 0.37 mm. (HPLC Method D).

The synthetic route of 6188-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BORZILLERI, Robert M.; LIU, Peiying; TEBBEN, Andrew J.; VELAPARTHI, Upender; RAHAMAN, Hasibur; TONUKUNURU, Gopikishan; WARRIER, Jayakumar Sankara; (264 pag.)WO2018/17633; (2018); 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.89284-61-7, name is 4-Chloronicotinonitrile, molecular formula is C6H3ClN2, molecular weight is 138, as common compound, the synthetic route is as follows.HPLC of Formula: C6H3ClN2

[00425] To a solution of 78-1 (500.0 mg, 3.6 mmol, 1.0 eq), 78-2 (581.5 mg, 3.6 mmol, 0.45 mL, 1.0 eq) and Cs2C03 (1.2 g, 3.6 mmol, 1.0 eq) in dioxane (10.0 mL) was added BINAP (224.7 mg, 0.36 mmol, 0.1 eq) and palladium acetate (81.0 mg, 0.36 mmol, 0.1 eq). The resulting mixture was stirred at 100 C under N2 for 15 hour. LCMS showed the desired compound was formed and the starting material was consumed completely. TLC (30% ethyl acetate in petroleum ether, Rf = 0.4) showed the starting material was consumed and a new spot appeared. The reaction mixture was concentrated. The crude residue was dissolved in CH2C12 (25 ml) and washed with water (2 x 15 mL). After drying over anhydrous Na2S04, the solvent was removed under reduced pressure to afford the crude product. The crude product was purified by column chromatography over silica gel to provide 78-3 (620.0 mg, 2.4 mmol, 65.3% yield). LCMS (ESI): RT = 0.575 min, mass calc. for Ci3H8F3N3 263.07, m/z found 263.8 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89284-61-7, 4-Chloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10235-65-1 ,Some common heterocyclic compound, 10235-65-1, molecular formula is C9H5Cl2N3, 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 (31 .8 mg, 0.796 mmol) was added to DMF (1 mL), followed by 3,4-dihydro-1 (2H)- isoquinolinone (107 mg, 0.730 mmol). The resulting suspension was stirred at r.t. for 5 min, then 4,6- dichloro-2-(2-pyridinyl)pyrimidine (150 mg, 0.664 mmol) was added and resulting mixture was stirred at r.t. for 45 min.The mixture was partitioned between EtOAc and water then the aqueous layer extracted with DCM three times. The organic layers were combined, filtered throught a phase separator and volatiles removed under reduced pressure to afford 212 mg of a white-brown powder.The crude material was purified by column chromatography, eluting with a 0 to 100% EtOAc in cyclohexane, to give the title compound, 121 mg (54%) as an off white powder.LCMS (Method A) Rt 1 .05 min, MH+=337.0

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. 10235-65-1, 4,6-Dichloro-2-(pyridin-2-yl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Stephen John; BARKER, Michael David; CAMPBELL, Matthew; HUMPHREYS, Philip; LIDDLE, John; SHEPPARD, Robert John; WILSON, David; WO2012/52390; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-81-9, 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.884494-81-9, name is 3-Bromo-5-fluoro-2-methoxypyridine, molecular formula is C6H5BrFNO, molecular weight is 206.01, as common compound, the synthetic route is as follows.

PREPARATION 10; (5-Fluoro-2-methoxypyridin-3-yl)boronic acid n-Butyllithium (1.6 M solution in hexanes, 20 mL, 32 mmol) was slowly added (0.4 mL/min) to a solution of 3-bromo-5-fluoro-2-methoxypyridine (6.0 g, 29.12 mmol) and triisopropylborate (8.4 mL, 36.62 mmol) in dry tetrahydrofuran (70 mL) at -100 C under argon atmosphere. The reaction mixture was stirred at -100 C for 2 hours and afterwards the temperature was allowed to warm up slowly overnight to ambient temperature before being cooled down to 0 C. Aqueous hydrochloric acid (1 N solution, 120 mL) was slowly added and the mixture was stirred at 0 C for 1 hour. A solution of sodium hydroxide (32% in water) was then added until pH was around 6 and the resulting mixture was extracted with diethyl ether (chi3). The combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound (3.28 g, 66%) as a white solid. X LRMS (m/z): 172 (M+1)+.1H-NMR delta (300 MHz, CDCI3): 4.04 (s, 3H), 6.00 (s, 2H), 7.88 (dd, 1 H), 8.09 (d,1 H).

The chemical industry reduces the impact on the environment during synthesis 884494-81-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ALMIRALL,S.A.; GONZALEZ RODRIGUEZ, Jacob; VIDAL JUAN, Bernat; VIDAL GISPERT, Laura; BACH TANA Jordi; WO2012/69202; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5223-06-3, 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 5223-06-3 as follows.

General procedure: To a solution of A1B1 (1.0mmol) and triphenylphosphine (1.5mmol) in anhydrous tetrahydrofuran (3mL), added C1 or C2 (2.0mmol) and dropwise added diethyl azodicarboxylate (DEAD, 1.5mmol) in anhydrous and anoxybiotic conditions. The reaction mixture was stirred at-2C for 30min, and then stirred at room temperature for 24h. After completion of reaction was monitored through TLC, the reaction mixture was filtered and washed with ether and saturated salt water to get products because there would be a solid precipitate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5223-06-3, its application will become more common.

Reference:
Article; Wang, Fang; Sun, Jun-Rong; Huang, Mei-Yan; Wang, Hui-Ying; Sun, Ping-Hua; Lin, Jing; Chen, Wei-Min; European Journal of Medicinal Chemistry; vol. 72; (2014); p. 35 – 45;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem