Day: September 26, 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.847375-33-1, name is Ethyl 2-(5-bromopyridin-3-yl)acetate, molecular formula is C9H10BrNO2, molecular weight is 244.0852, as common compound, the synthetic route is as follows.Recommanded Product: 847375-33-1

Step 9: 3-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid benzyl ester (1.96 g, 3.7 mmol), (5-bromo-pyridin-3-yl)-acetic acid ethyl ester (0.99 g, 4.1 mmol), and potassium carbonate (1.79 g, 13.0 mmol) were combined in DME (40 mL) and H2O (30 mL), and the solution was purged with N2 for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.427 g, 0.37 mmol) was added, and the reaction was stirred at 70 C. overnight. The mixture was quenched with 1N aqueous HCl(13 mL) and extracted with EtOAc. The combined organic layers were washed with H2O, and then dried and concentrated to give 3-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-carboxymethyl-pyridin-3-yl)-benzoic acid benzyl ester.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,847375-33-1, Ethyl 2-(5-bromopyridin-3-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; US2010/81673; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-82-3, 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. 153034-82-3, name is 2-Fluoro-4-iodonicotinaldehyde. A new synthetic method of this compound is introduced below.

a) Hydrazine monohydrate (0.78 mL, 15.94 mmol) was added dropwise to a suspension of 2-fluoro-4-iodonicotinaldehyde (2.00 g, 7.97 mmol) in 2-propanol (20 mL) and heated at 60 C. After 2 h, the solvent was removed by rotatory evaporation and the residue dissolved in EtAcO (40 mL) and washed with water (30 mL). The organic layer was dried over anhydrous Na2S04 and filtered. After removal of the solvent, the residue was purified by column chromatography on silica gel (10D40% EtAcO/hexanes), affording 1 .62 g of 4-iodo-1 H-pyrazolo[3,4-b]pyridine, [Rf= 0.30 (20% EtAcO/hexanes), white solid, 82% yield].LC-MS ESI+ m/z: 246 (M+1 , 99%) (Method 5).1 H-NMR (CDCI3, 250 MHz, ?) : 12.45 (br s, 1 H); 8.23 (d, J= 5.0 Hz, 1 H, ArH); 7.98 (s, 1 H, ArH); 7.61 (d, J= 5.0 Hz, 1 H, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-82-3, 2-Fluoro-4-iodonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; DRACONIS PHARMA, S.L.; ALMIRALL, S.A.; TORRENS JOVER, Andoni; MERCE VIDAL, Ramon; CALDENTEY FRONTERA, Francesc Xavier; RODRIGUEZ GARRIDO, Antonio, David; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/37960; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 100-54-9, Adding some certain compound to certain chemical reactions, such as: 100-54-9, name is Nicotinonitrile,molecular formula is C6H4N2, 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 100-54-9.

EXAMPLE 28 3-Pyridinecarboxamidine hydrochloride To a solution of 3-cyanopyridine (208 g, 2.0 mol) in methanol (100 ml) in an ice-bath was added sodium methoxide (11.2 g, 0.2 mol). The reaction mixture was stirred until all of the sodium methoxide had dissolved and was subsequently stoppered and placed in the refrigerator for 96 hours. Ammonium chloride (118 g, 2.2 mol) was then added and the reaction mixture was stirred in an ice-bath for 8 hours, followed by room temperature for 24 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was taken up in boiling ethanol (2 l), the solution was filtered and cooled to cause precipitation. The solid was collected by filtration and recrystallized in boiling n-propanol (1.4 l) to afford 153 g of a white solid. The filtrates were combined, concentrated in vacuo and the residue was recrystallized from n-propanol to afford 17.5 g of a white solid. The filtrate was once again concentrated in vacuo and the residue was recrystallized from n-propanol (500 ml) to afford 73 g of a white solid. The three crops were combined to afford 243.5 g (78%) of 3-pyridinecarboxamidine hydrochloride, m.p. 185-190 C. when dried at 60 C. in high vacuum.

According to the analysis of related databases, 100-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sterling Winthrop Inc.; US5294612; (1994); A;,
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. 17282-04-1, name is 2-Chloro-3-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H3ClFN

A solution of 2-chloro-3-fluoropyridine (2 mmol) in anhydrous THF (10ml) was cooled to -780C. To this solution was added a solution of lithium diisopropylamide (LDA; 2.2 mmol) in hexane slowly at same temperature. After 2h at -780C, to the mixture was added trimethoxyborane (0.48ml) and stirred for 2h, followed by an addition of peracetic acid (0.72 ml; 32% in dilute acetic acid). The mixture was allowed to warm to O0C under stirring for Ih, then cooled to -2O0C, sodium dithionite (0.8g in 2ml water) was added dropwise. The mixture was extracted with ethyl acetate and the extract was dried and concentrated. The residue was purified by chromatography, eluting with 1:19 MeOH:DCM to give the expected product as a white solid (80%).

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, 17282-04-1, 2-Chloro-3-fluoropyridine.

Reference:
Patent; BTG INTERNATIONAL LIMITED; WO2009/103950; (2009); 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. 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-6-methoxypicolinic acid

To a solution of 5-bromo-6-methoxypyridine-2-carboxylic acid (500 mg, 2.15 mmol, 1.00 eq.) insulfuric acid (10 mL) in ice bath was added HNO3 (5 mL) dropwise. The resulting solution was allowed to stir at 60 C for 16 h. After being cooled to rt, the solution was poured into ice/water (20mL). The solids were collected by filtration to provide 3-amino-5-bromo-6-methoxypyridine-2- carboxylic acid as a light yellow solid (260 mg, 44%). LCMS (ES) [M-1] mlz 275.0.

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, 1214334-70-9, 5-Bromo-6-methoxypicolinic acid.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; YU, Ming; LI, Zhe; XU, Qing; YEE, Calvin; SETTI, Lina; SHAM, Hing; (188 pag.)WO2019/36384; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 626-60-8, 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 626-60-8, name is 3-Chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A. 3-Chloro-N-(4-chlorophenyl)pyridine-4-carboxamide. A solution of 3-chloropyridine (1.00 mL, 10.5 mmol) in THF at -78 C. was treated dropwise with a solution of lithium diisopropylamide in THF [freshly prepared by addition of butyllithium (7.21 mL, 11.5 mmol) to diisopropylamine (11.5 mmol)]. After 0.25 h, the mixture was treated with carbon dioxide(g) and slowly warmed to ambient temperature. The mixture was concentrated, partitioned between EtOAc and water, and the aqueous layer was washed with EtOAc (2*). The pH of the aqueous layer was adjusted (~3) by addition of 1 N HCl and then washed with EtOAc (3*). The combined extracts were dried with magnesium sulfate and concentrated. The residue was recrystallized from EtOAc yielding 200 mg (12%) of 3-chloroisonicotinic acid.

According to the analysis of related databases, 626-60-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US6610704; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1003-68-5, 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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, 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.

5-methyl-2-pyridone (2) (20 g, 0,18 mol), K2C03 (30,4 g, 0,22 mol), NaOAc (3 g, 0,036 mol, 0,2 mol eq), CuBr (2,62 g, 0,018 mol, 0.1 mol eq) [or Cu20 (1 ,29 g, 0,05 mol eq)], Bromobenzene (4) (40,28 g, 0,26 mol, 1 ,4 mol eq) and DMSO (10 mL, 0,5 V eq) was placed in a round bottom flask under a nitrogen atmosphere. Flask was heated to 135-140C and stirred at this temperature for 6-8 h. After the completion of the reaction according to HPLC analysis, reaction medium was cooled down to about 60 C. Then, 100 mL water was added to the reaction mixture followed by 4 mL NH4OH and 100 mL toluene. The resulting mixture was stirred for 15 min and the phases were separated. Aqueous phase was extracted with 2×50 mL toluene then organic phases were combined (all extractions were carried out at about 60C). Combined organic phases were filtered over a bed of celite after treatment with charcoal. After evaporation of toluene to the dryness, 36,3 g crude pirfenidone was obtained. Crude pirfenidone purity is >99,5% (HPLC analysis, UV detector 310 nm).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Patent; ULKAR KIMYA SANAYII VE TICARET A. S.; KOYUNCU, Hasan; AKGOL, Emre; REIS, Omer; (16 pag.)WO2016/122420; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71935-32-5, 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. 71935-32-5, name is 4-(Hydroxymethyl)picolinonitrile. A new synthetic method of this compound is introduced below.

In toluene, 4-hydroxymethylpyridine-2-carbonitrile (111 mg, 0.83 mmol) synthesized in Production Example 87 was dissolved, and thionyl chloride (73 muL) was added thereto. The mixture was refluxed for 30 minutes. Thereafter, the mixture was allowed to cool down to a room temperature and stirred for one hour. After the completion of the reaction was confirmed by HPLC, the solvent was distilled off. The resulting residue was used for the next reaction without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71935-32-5, its application will become more common.

Reference:
Patent; ASKA Pharmaceutical Co., Ltd; Okada, Makoto; Hasumi, Koichi; Nishimoto, Takahiro; Yoshida, Miwa; Ishitani, Kouki; Aotsuka, Tomoji; Kanazawa, Hashime; US2013/85127; (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 13602-11-4, name is Methyl 6-methylpyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 13602-11-4

Step 3 in N2 condition, compound 3 (10g, 66.2mmol), CCl4(100 ml), NBS is sequentially added in the solution (17.7g, 99 . 3mmol), AIBN (543.5 mg, 3 . 3mmol), reflux reaction 12h, after detecting reaction is complete, concentrated under reduced pressure, by adding water, extraction with ethyl acetate, combined with the phase, ethyl acetate is removed under reduced pressure, the oily compound crocatus obtained. Recrystallization with petroleum ether and ethyl acetate (10:1) finally obtaining the white solid compound 4 (7.8g), yield 51.3%. This step attempts to adopt different post-processing method, of column chromatography, recrystallization effect is not good, and recrystallization to obtain product is a white solid, no other color.

With the rapid development of chemical substances, we look forward to future research findings about 13602-11-4.

Reference:
Patent; Shanghai Institute Of Technology; Yao, Zhiyi; Zhang, Xiaopan; Zong, Haoqiang; Wang, Dongsheng; (14 pag.)CN105294552; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 104830-06-0, 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. 104830-06-0, name is 2-Amino-3-iodopyridine. A new synthetic method of this compound is introduced below.

General procedure: 2-Iodoaniline 2a (65.7 mg, 0.3 mmol), Cu(OAc)2 (6 mg, 10%), KOtBu (101 mg, 0.9 mmol), DMAc (1.0 mL) were mixed in a Schlenck tube and then to the mixture was added 2-(phenylethynyl)benzonitrile1a (74 mg, 0.36 mmol) under N2. The reaction mixture was stirred for 12 h at 120 C under N2. After the reaction was completed (monitored by TLC), the reaction mixture was then diluted with water and extracted with ethyl acetate. After the combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure, the residue was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate as eluent to afford the pure product 3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,104830-06-0, its application will become more common.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem