Day: August 3, 2021

Synthetic Route of 586-95-8 ,Some common heterocyclic compound, 586-95-8, molecular formula is C6H7NO, 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.

(IV) 4-Chloromethylpyridine hydrochloride (19) STR16 4-Hydroxymethylpyridine (18) 54.4 g (0.50 mol) was dissolved in acetonitrile 202 ml. The solution was added dropwise to the mixture of thionyl chloride 65.3 g (0.55 mol) and acetonitrile 109 ml under 50 C. The mixture was stirred at the same temperature for 1 hour, then cooled to room temperature to yield the slurry (quantitative) of the objective (19). 1 H-NMR (DMSO-TMS) delta ppm: 5.09 (s, 2H), 8.09 (d, J=6.6 Hz, 2H), 8.94 (d, J=6.6 Hz, 2H),

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,586-95-8, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; US6057448; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17228-69-2, 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. 17228-69-2, name is 2-Chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

Ethanolamine (4.0 ml) was added to potassium tert-butoxide (96 ml of a 1M solution in THF) and the reaction was stirred at room temperature for 30 min. 2-Chloro-4- methoxypyridine was added dropwise and the reaction mixture was heated under reflux for 16 h. The reaction mixture was cooled, filtered and evaporated to an oil. This was dissolved in xylene (100 ml) and treated with toluene-4-sulphonic acid (50 mg) and heated under reflux for 16 h. More toluene-4-sulphonic acid (50 mg) was added and the heating was continued for a further 16 h under reflux. The mixture was concentrated, the residue was passed through a pad of silica and eluted with 5% 7M ammonia in methanol/DCM to give the sub-title compound as a brown oil (5.0 g). MS APCI +VE/Z 169 ([M+H]). 1H NMR 300MHz (DMSO-d6) 7.76 (1H, d), 6.33 (1H, t), 6.13-6. 10 (1H, m), 5.99 (1H, m), 3.70 (3H, s), 3.54-3. 47 (2H, m), 3.31-3. 25 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17228-69-2, 2-Chloro-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2004/87666; (2004); A1;,
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. 5345-47-1, name is 2-Aminonicotinic acid, molecular formula is C6H6N2O2, 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. COA of Formula: C6H6N2O2

2-Aminonicotinic acid (10.00 g, 72.40 mmol) was suspended in 40 ml of glacial acetic acid. To this suspension was added dropwise a solution of 4.82 ml (94.12 mmol) of bromine in 20 ml of glacial acetic acid. The mixture was stirred vigorouly at room temperature for 30 min. The formed precipitate was filtered off and washed with glacial acetic acid. The filter cake was collected and crystallized from the boiling methol to afford compound 8 as a white solid (14.5 g, 92% yield). 1H NMR (300 MHz, DMSO-d6) delta 8.30 (d, J = 2.4 Hz, 1H), 8.16 (d, J = 2.4 Hz, 1H); MS (ESI, m/z): 216.8 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 5345-47-1.

Reference:
Article; Zhang, Dengyou; Ai, Jing; Liang, Zhongjie; Li, Chunpu; Peng, Xia; Ji, Yinchun; Jiang, Hualiang; Geng, Meiyu; Luo, Cheng; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5169 – 5180;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 10165-86-3, Methyl 6-formylnicotinate, 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, 10165-86-3, blongs to pyridine-derivatives compound. COA of Formula: C8H7NO3

A mixture of methyl 6-formylnicotinate (1.000 g, 6.055 mmol) and 3-chloro-4-fluoroaniline (0.970 g, 6.66 1 mmol) in tetrahydrofuran (50 mL) was stuffed at the room temperature for 30 mm, and treated with sodium triacetoxyborohydride (1.925 g, 9.083 mmol). The reaction mixture was stuffed at the same temperature for additional 18 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 40 g cartridge; ethyl acetate / dichloromethane = 0 percent to 5 percent) to give methyl6-(((3-chloro-4-fluorophenyl)amino)methyl)nicotinate as brown solid (0.510 g, 28.6percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10165-86-3, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); 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.884494-34-2, name is 2-Ethynyl-5-fluoropyridine, molecular formula is C7H4FN, molecular weight is 121.11, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Step 3: Preparation of ethyl 5-(5-fluoropyridin-2-yl)isoxazole-3-carboxylate To a solution of 2-ethynyl-5-fluoropyridine (1.5 g, 12.4 mmol) in N,N-dimethylformamide (20 mL) at 23 C. was added (Z)-Ethyl 2-chloro-2-(hydroxyimino)acetate (2.81 g, 18.6 mmol). The reaction mixture stirred for 1 h before triethylamine (1.88 g, 18.6 mmol) was added. The mixture was heated at 90 C. for 16 h. The mixture was diluted with brine (100 mL), extracted with ethyl acetate (100 mL*2) and purified by column chromatography (silica, petroleum ether/ethyl acetate=20/1) to give ethyl 5-(5-fluoropyridin-2-yl)isoxazole-3-carboxylate (300 mg, 1.27 mmol, 10%) as a gray oil. LCMS (ESI) m/z: 237.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-34-2, 2-Ethynyl-5-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 87394-65-8 , The common heterocyclic compound, 87394-65-8, name is 1-(5-Chloro-2-pyridyl)piperazine, molecular formula is C9H12ClN3, 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 solution of triphosgene (300 mg) in CH2CI2 (5 mL) was added 1- phenylpiperidin-4-ol (352 mg, 1.99 mmol) over 3 hr, followed by the addition of a solution of 5-[(tert-butyldimethylsilyl)oxy]pyridin-2-amine (448 mg, 2.00 mmol, 1.00 eq) in pyridine (1 mL) over 16 hr. The resulting solution was stirred an additional 16 h at rt, then extracted with 2×30 mL of CH2CI2. The combined organic layers were concentrated under vacuum and purified with silica gel chromatography using CH2CI2 / MeOH (20: 1) to afford 270 mg (32%) of the title compound as an off-white solid. LC-MS: (ES, m/z) 428.

The synthetic route of 87394-65-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTAURUS THERAPEUTICS; ROMERO, Donna, L.; BLITZER, Jeremy; (242 pag.)WO2019/140188; (2019); 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. 13466-38-1, name is 5-Bromopyridin-2-ol. A new synthetic method of this compound is introduced below., Formula: C5H4BrNO

Synthesis of 5-bromo-2-(2-methoxyethoxy)pyridineTo a solution of 5-bromopyridin-2-ol (5.75 mmol, lg), triphenylphosphine (8.62mmol, 2.26 g), and 2-methoxyethanol (7.2 mmol, 0.55 g) in THF (25 mL), was added slowly diisopropyl azodicarboxylate (8.62 mmol, 1.7 mL) at RT. The mixture was stirred at RT overnight. The reaction was quenched with MeOH, diluted with water and extracted with DCM (25 mL). The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Crude was purified by flash chromatography (cyclohexane/EtOAc = 9/2 -> 7/3) to yield title product. Y: 1.05 g (79%), P>80%, rt=3.9 min (gradient A), (M+H)+ = 233.

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, 13466-38-1, 5-Bromopyridin-2-ol.

Reference:
Patent; EUROSCREEN S.A.; HOVEYDA, Hamid; DUTHEUIL, Guillaume; EL BOUSMAQUI, Mohamed; BERNARD, Jerome; WO2011/151434; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1150618-36-2, 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.1150618-36-2, name is 5-Bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H4BrF3N2, molecular weight is 265.03, as common compound, the synthetic route is as follows.

A mixture of 5-bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (0.250 g, 0.943 mmol), phenylmethanethiol (0.122 mL, 1.038 mmol), DIEA (0.329 mL, 1.887 mmol), Pd2(dba)3 (43.19 mg, 47.16 mumol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (54.58 mg, 94.33 mumol) in dioxane (10 mL) was stirred for 1 hour and heated to 150 C for 2 hours under microwave conditions. The mixture was cooled to RT and taken up in EtOAc. The organic layer was washed with NaHCO3(3x) and brine, dried (MgSO4), filtered and concentrated. The residue was purified via column chromatography (1:1EtOAc/hexane) to give the title compound as a yellow solid (0.78g, 95% yield). LCMS m/z = 309.4[M+H]+.

The chemical industry reduces the impact on the environment during synthesis 1150618-36-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; TRAN, Thuy-Anh; ULLMAN, Brett; KRAMER, Bryan Aubrey; DO, Quyen-Quyen Thuy; SHIN, Young-Jun; (202 pag.)WO2019/113359; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 920979-04-0, 2-Iodo-6-(trifluoromethyl)pyridin-3-amine, 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 2-Iodo-6-(trifluoromethyl)pyridin-3-amine, blongs to pyridine-derivatives compound. Quality Control of 2-Iodo-6-(trifluoromethyl)pyridin-3-amine

A solution of 2-iodo-6-(trifluoromethyl)pyri din-3 -amine (1.1 g, 3.82 mmol), triethylamine (1.60 mL, 11.5 mmol), palladium (II) acetate (231 mg, 1.03 mmol), tri(o- toly)lphosphine (86 g, 2.06 mmol), and methyl prop-2-enoate (1.6 g, 18.59 mmol, 5.00 equiv) in acetonitrile (100 mL) stirred overnight at 90 C in an oil bath. The resulting mixture was concentrated under vacuum. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate, and the combined organic phases were washed with 50 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1 :3 ethyl acetate/petroleum ether) to give methyl (2E)-3-[3-amino-6- (trifluoromethyl)pyridin-2-yl]prop-2-enoate (900 mg, 96%) as a yellow solid. MS: (ESI, m/z): 247[M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,920979-04-0, 2-Iodo-6-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone, the common compound, a new synthetic route is introduced below. Recommanded Product: 53937-02-3

To a solution of Compound 11 (1 g, 4.97 mmol) in DMF (10 mL) was slowly added sodium hydride (219 mg, 5.47 mmol) under ice-cooling, and the obtained reaction mixture was stirred under ice-cooling for 45 minutes. Methyl 2-bromopropionate was added dropwise thereto, and the obtained reaction mixture was warmed up to room temperature and then stirred overnight. To the reaction liquid was added water, followed by extraction with ethyl acetate. The organic layer was washed twice with water and then dried with magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The concentrated residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1 to 1:4) to obtain Compound 12 (1.03 g, 72%) as a yellow solid. Compound 12; 1H-NMR (CDCl3) delta: 1.62 (3H, d, J=7.60 Hz), 3.75 (3H, s), 4.99 (2H, s), 5.54 (1H, q, J=7.44 Hz), 5.99 (1H, d, J=2.53 Hz), 6.04 (1H, dd, J=7.60, 2.53 Hz), 7.19 (1H, d, J=7.60 Hz), 7.35-7.40 (5H, m).

The synthetic route of 53937-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; Kojima, Eiichi; Tonogaki, Keisuke; Tanaka, Nobuyuki; Katou, Manabu; Ino, Akira; Iwatsu, Masafumi; Fujioka, Masahiko; Hinata, Yu; Ohyabu, Naoki; (119 pag.)US9567330; (2017); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem