Pyridine-derivatives

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

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 86847-59-8, name is 2,2-Dimethyl-N-pyridin-2-yl-propionamide, the common compound, a new synthetic route is introduced below. Recommanded Product: 2,2-Dimethyl-N-pyridin-2-yl-propionamide

To a mixture of 2,2-dimethyl-N-pyridin-2-yl-propionamide (3.0 g, 17 mmol) described in Manufacturing Example 39-1-1, N,N,N’,N’-tetramethylethylenediamine (6.3 mL, 42 mmol) and tetrahydrofuran (60 mL) was added dropwise n-butyl lithium (1.6 M n-hexane solution, 30 mL, 47 mmol) at -78 C., which was stirred overnight at 0 C. Iodine (6.8 g, 27 mmol) was added to the reaction mixture at -78 C., and stirred for 1.5 hours at 0 C. Water and saturated aqueous sodium thiosulfate solution were added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate_heptane=2:1) to obtain the title compound (2.9 g, 57%). 1H-NMR Spectrum (CDCl3) delta (ppm): 1.38 (9H, s), 6.85 (1H, dd, J=4.8, 7.9 Hz), 7.94 (1H, brs), 8.11 (1H, dd, J=1.7, 7.9 Hz), 8.46 (1H, dd, J=1.7, 4.6 Hz).

The synthetic route of 86847-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 38533-61-8, 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. 38533-61-8, name is 2-Chloro-6-methoxy-3-nitropyridine. A new synthetic method of this compound is introduced below.

A solution of 2-chloro-6-methoxy-3-nitropyridine (1.0 g, 5.3 mmol) in EtOH (50 ml)/EtOAc (50 ml) is hydrogenated at RT and 40 psi, in the presence of 10% Pd-C (0.394 g, 0.37 mmol). The suspension is filtered through cellulose and washed with EtOH. The solution is concentrated under vacuum to give a brown oil 0.58 g (69% yield) that is used without further purification in the next step. MS (ESI+) for C6H7ClN2O m/z 159.0 (M+H)+. Example 310 (from 2-chloro-6-methoxypyridin-3-amine and 2-isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole) is prepared by following Method C, making non-critical modifications. The solid is triturated with CH2Cl2 to give a white solid 0.104 g (47% yield). HRMS (ESI) calcd for C10H7N5O2SClF3+H 354.0039, found 354.0046.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38533-61-8, 2-Chloro-6-methoxy-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 36404-90-7, 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. 36404-90-7, name is 2-Fluoro-3-formylpyridine, molecular formula is C6H4FNO, 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.

Add 50g of intermediate 1-1 to a 1L three-necked flask.19.0 g of intermediate 6-1,29.3g potassium carbonate,30g 4A molecular sieve,500ml acetonitrile,The temperature was raised to 80 C and the reaction was stirred for 10 h.TLC monitors the raw materials to complete room temperature and then drops to room temperature.The reaction mixture was concentrated by filtration. The obtained crude crystals were evaporated to dryness.

According to the analysis of related databases, 36404-90-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Liu Kaipeng; Zhang Hongke; Guo Jing; Wang Xiaowei; Liu Qianfeng; Gao Renxiao; (35 pag.)CN109293583; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89284-11-7, 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. 89284-11-7, name is 5,6-Dibromopyridin-2-amine, molecular formula is C5H4Br2N2, 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.

A mixture of 5,6-dibromopyridin-2-amine (80 g, 318 mmol), ethynylbenzene (78 ml, 698 mmol), copper(I) iodide (1.51 g, 7.94 mmol), Dichlorobis(triphenylphosphine)- palladium(II) (5.79 g, 7.94 mmol) and triethylamine (110 ml, 794 mmol) is stirred under argon atmosphere in ACN (500 ml) with THF (250 ml) for 21 h at 50C. The mixture is diluted with water and extracted with DCM. The combined organic layers are dried over MgS04, concentrated in vacuo and the product purified by NP chromatography. Yield: 82 g (94%). HPLC-MS: M+H=273/275; tR=1.34 min (*Method_l).

According to the analysis of related databases, 89284-11-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; BADER, Gerd; SPEVAK, Walter; STEFFEN, Andreas; PARKES, Alastair L.; WO2013/127729; (2013); A1;,
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 69950-65-8, name is Methyl 6-formyl-2-pyridinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 69950-65-8

General procedure: To a solution of 3-bromo-2-phenyl-7-(trimethylsilyl)pyrazolo[1,5-a]pyridine (18, 550 mg, 1.59 mmol) in THF (4 mL) was added n-butyllithium (0.7 mL, 1.91 mmol, 2.6 mol/L solution in hexane) at -78 C. After stirring at -78 C for 0.5 h, a solution of methyl 6-formylpicolinate (527 mg, 3.19 mmol) in THF (4 mL) was added to the mixture at -78 C. The solution was stirred at room temperature for 1 h, and then the reaction was quenched by the addition of saturated aq. ammonium chloride. The mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (hexane:AcOEt = 4:1) to give the title compound 23 as a yellow oil (361 mg, 53%).

With the rapid development of chemical substances, we look forward to future research findings about 69950-65-8.

Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Saito, Yoshifumi; Watanabe, Hiroyuki; Kondo, Tatsuhiro; Kondo, Atsushi; Kawamura, Naohiro; Tatani, Kazuya; Kohno, Yasushi; Tanaka, Nobuyuki; Seto, Shigeki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 17; (2017); p. 4044 – 4050;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem