Category: pyridine-derivatives

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 19524-06-2, name is 4-Bromopyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H5BrClN

In a Schlenk flask under argon 4-bromo-5-methylthiophene-2-ylboronicacid (3.2 g, 14.14 mmol) was dissolved in THF (25 mL) and degassed.4-bromopyridine hydrochlorid (4.43 g, 22.68 mmol), Pd(dppf)Cl2(740 mg, 0.91 mmol) and aq Na2CO3 solution (20percent, 25 mL) wereadded and the mixture was stirred under reflux overnight at 80 °C.The reaction mixture was extracted three times with DCM, the combined organic phases werewashed with water and brine, dried over MgSO4, filtered and the solvents was removed underreduced pressure. Purification by flash column chromatography (pure cyclohexane + 1percentNEt3) afforded a brownish solid with a yield of 51percent.

With the rapid development of chemical substances, we look forward to future research findings about 19524-06-2.

Reference:
Article; Sarter, Christopher; Heimes, Michael; Jaeschke, Andres; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1103 – 1110;,
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. 885588-12-5, name is 2-Bromo-5-fluoro-4-pyridinecarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Bromo-5-fluoro-4-pyridinecarboxylic acid

A mixture of 2-bromo-5-fluoroisonicotinic acid [885588-12-5] (1.00 g, 4.55 mmol), (li?)-l- methyl-l,2,3,4-tetrahydroisoquinoline [84010-66-2] (803 mg, 5.45 mmol), HATU (2.34 g, 6.14 mmol) and DIPEA (2.34 mL, 13.5 mmol) in DMF (50 mL) was stirred at rt for 20 h. The reaction mixture was diluted with EtOAc and brine. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried over MgS04, filtered and evaporated in vacuo. The crude mixture was purified by preparative LC (irregular SiOH, 15-40 mih, 80 g Grace, liquid injection (DCM), mobile phase gradient: heptane / EtOAc from 90: 10 to 0: 100) to afford intermediate 113 (1.62 g, quant.).

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, 885588-12-5, 2-Bromo-5-fluoro-4-pyridinecarboxylic acid.

Reference:
Patent; JANSSEN SCIENCES IRELAND UNLIMITED COMPANY; LANCOIS, David Francis Alain; GUILLEMONT, Jerome Emile Georges; RABOISSON, Pierre Jean-Marie Bernard; RIGAUX, Peter; MICHAUT, Antoine Benjamin; QUATREVAUX, Sabrina Dany France; SOVY, Chao; ROYMANS, Dirk Andre Emmy; (99 pag.)WO2019/206828; (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. 1010120-55-4, name is 5-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine

4-[ 4-( 4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzyl]-thiomorpholine-1, 1-dioxide(1.1eq.) was added to a solution of 5-bromo-[1,2,4]triazolo[1,5-a]pyrid in-2-ylamine (4:1). K2C03 (2eq.) and PdCbdppf (0.03 eq.) were added to the solution. The resulting mixture was then heated in anoil bath at 90C for 16h under N 2. Water was added and the solution was extracted with ethyl acetate.The organic layers were dried over anhydrous MgS04 and evaporated in vacuo. The final compoundwas obtained after purification by flash chromatography.[00162] 1H (400 MHz, CDCh) 8 7.94-7.92 (d, 2H), 7.52-7.48 (m, 3H), 7.37-7.34 (m, 1H), 7.02-7.00(m, 1H), 6.00 (d, 2H), 3.76 (d, 2H), 3.15-3.13 (m, 4H), 2.93-2.91 (m, 4H).[00163] m/z 358.2 (M+H+, 100%).

The synthetic route of 1010120-55-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; VAN ‘T KLOOSTER, Gerben Albert Eleutherius; BRYS, Reginald Christophe Xavier; VAN ROMPAEY, Luc Juliaan Corina; NAMOUR, Florence Sylvie; WO2013/189771; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1403257-80-6, 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. 1403257-80-6, name is 5-Bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzamide, molecular formula is C23H30BrN3O3, 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.

Step 1: Synthesis of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-5-(6-formylpyridin-3-yl)-2-methylbenzamide To a stirred solution of 5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzamide (1 g, 2.15 mmol) and (6-formylpyridin-3-yl)boronic acid (0.539 g, 2.31 mmol) in dioxane/water mixture (15 mL+3 mL), Na2CO3 (0.82 g, 7.74 mmol) was added and solution purged with argon for 15 min. Then Pd (PPh3)4 (0.288 g, 0.25 mmol) was added and argon was purged again for 10 min. Reaction mass was heated at 80 C. for 2 h. On completion, reaction mixture was diluted with water and extracted with 10% MeOH/DCM. Combined organic layers were dried over Na2SO4 and solvent removed under reduced pressure to afford crude material which was purified by column chromatography over silica gel to afford the desired compound (0.60 g, 57%).

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 1403257-80-6, 5-Bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzamide.

Reference:
Patent; KUNTZ, KEVIN W.; CHESWORTH, RICHARD; DUNCAN, KENNETH W.; KEILHACK, HEIKE; WARHOLIC, NATALIE; KLAUS, CHRISTINE; ZHENG, WANJUN; SEKI, MASASHI; SHIROTORI, SYUJI; KAWANO, SATOSHI; US2012/264734; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1597-32-6, 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 1597-32-6, name is 2-Amino-6-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 20: 1-(4-Fluorophenyl)-/V-(6-fluoro-2-pyridinyl)-5-methyl-1H-1 ,2,3-triazole- 4-carboxamide; To a solution of 6-fluoro-2-pyridinamine (0.092 g, 0.822 mmol) in dry 1 ,4-dioxane (1 ml) was added dropwise trimethylaluminium (0.401 ml, 0.802 mmol) (2M solution in toluene). The solution was stirred at room temperature for 30 min. Then a solution of ethyl 1-(4-fluorophenyl)-5-methyl-1 H-1 ,2,3-triazole-4-carboxylate (Intermediate 2) (0.05 g, 0.201 mmol) in dry 1 ,4-dioxane (1 ml) was added at room temperature and the reaction was heated to 100 0C for 1.5 hours. The reaction was cooled to room temperature, quenched cautiously with water (0.06 ml), and stirred at room temperature for 10 min. Then, sodium sulphate (0.25 g) was added to bind the water and the mixture was stirred vigorously for 5 min. Dichloromethane was added and the mixture was stirred for an additional 10 min at room temperature. The solution was filtered and the solid was washed with dichloromethane. The filtrate was evaporated to afford a residue. The residue was partially dissolved in methanol, filtered and the solid washed with diethyl ether to afford a the title compound (44.5%); MH+= 316; 1HNMR (DMSO, 400 MHz): 2.57 (3H s), 6.96 (1 H m), 7.53 (2H t), 7.76 (2H m), 8.07 (2H m), 10.22 (1 H s).

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 1597-32-6, 2-Amino-6-fluoropyridine.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/115486; (2009); 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. 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride

[0091 ] In a four necked round bottomed flask, under nitrogen atmosphere, 1000 ml acetonitrile, 49.5 gm of 5,6,7, 7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one.HCl, 55 gm of sodium carbonate and 100 gm of Methyl (R)-2- (4-nitrophenylsulfonyloxy)-2(2- chlorophenyl)acetate were added and the mixture was heated to about 50C. After reaction, reaction mass was filtered, filtrate concentrated and concentrated mass was taken in dichloromethane, washed with water and concentrated under reduced pressure. The oily residue was treated with IPA.HC1 solution in isopropanol (IPA) and filtered to obtain the mixture of isomers as hydrochloride salt. To it sodium bicarbonate solution was added till pH turned alkaline. The product was then extracted in dichloromethane (MDC). The MDC layer was washed with water, dried and distilled to obtain the product as an oily residue. [0092] Ratio of (7aS,2’S)/(7aR,2’S)-isomers as per chiral HPLC : 53.62/46.38% : [0093] Example 2. Methyl (7aS,2’S)-2-(2-chlorophenyl)-2-(2,4,5,6,7,7a-hexahydro thieno[3,2-c]-5-pyridin-2-one)acetate [0094] In a four necked round bottomed flask, under nitrogen atmosphere, 150 ml of ethyl acetate-methanol and 70 gm of mixture of isomers (Ratio of (7aS,2’S)/(7aR,2’S)-isomers = 53.62:46.38) was taken and warmed to dissolve, and stirred for 20 hours under room temperature, crystals obtained were filtered and the solid was dried to obtain 52 gm Methyl (S)-2(2-chlorophenyl)-2-(2,4,5,6,7,7a-hexahydrothieno[3,2-c]-5-pyridin-2-one) acetate. Yield = 60%; Ratio of (7aS,2’S)/(7aR,2’S)-isomers as per chiral HPLC : 99.5:0.5. [0095] .H-NMR(DMSO-d6) spectra collected on a BRUKER 400MHz instrument has shown values given in table 2 corresponding to structure of formula II A free base below: [0096] Table 2: No. m- multiplet, s-singlet, d-doublet of doublet. Single crystal analysis data of material conforms to (7aS,2″S)-conl”iguration.

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, 115473-15-9, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride.

Reference:
Patent; IPCA LABORATORIES LIMITED; KUMAR, Ashok; SOUDAGAR, Satish Rajanikant; NELLITHANATH, Thankachen Byju; SAHAL, Gaurav; MATHUR, Arpana Prashant; GAWADE, Sanjay Pandurang; BHADRA, Dinesh Kanji; MOJE, Devki; WO2013/1544; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84249-14-9, 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 84249-14-9, name is 2-Amino-4-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 4-bromopyridin-2-amine (3.11 g, 17.98 mmol) in CH2CI2 (60 mL) at 0 C was added acetyl chloride (1.406 mL, 19.77 mmol) and pyridine (1.745 mL, 21.57 mmol). The mixture was warmed to rt and stirred for 2 h. The reaction was quenched with water and diluted with EtOAc. The layers were separated. The organic layer was washed with water, brine, dried Na2S04) and concentrated under reduced pressure to obtain N-(4-bromopyridin-2-yl)acetamide (3.82 g, 17.05 mmol, 95% yield) as a white solid. The material was carried on without further purification. LCMS (ESI) m/e 215.0 [(M+H)+, calcd 215.0]; LC/MS retention time (method A): /R = 2.61 min.

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 84249-14-9, 2-Amino-4-bromopyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6602-32-0, 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. 6602-32-0, name is 2-Bromo-3-hydroxypyridine, molecular formula is C5H4BrNO, 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.

To a stirred solution of triphenylphosphine (6.31 g, 24.1 mmol) and DEAD (4.49, 25.8 mmol) in THF (30 mL) at 0 Cwas added a solution of 3 (3.10 g, 17.2 mmol) and 2-bromopyridin-3-ol 4 (3.44 g, 19.8 mmol) in THF (20 mL). The resulting luminous yellow solution was stirred under a nitrogen atmosphere at ambient temperature for 24 h at which all starting materials had been consumed. The solvent was removed, the residue was purified by flash chromatography on silica gel eluting with EtOAc/petroleum ether (1%-20%) to give 5 as light yellow liquid (4.97 g, 86%). 1H NMR (400 MHz, DMSO-d6) delta 8.06 (s, ArH, 1H), 7.92 (dd, J = 1.2, ArH, 4.4 Hz, 1H), 7.88 (d, J = 7.6 Hz, ArH, 1H), 7.72 (d, J = 7.6 Hz, ArH, 1H), 7.54 (t, J = 7.8 Hz, ArH, 1H), 7.45 (dd, J = 1.2, 8.0 Hz, ArH, 1H), 7.29 (dd, J = 4.8, 8.0 Hz, ArH, 1H), 5.84 (q, J = 6.4 Hz, CH, 1H), 3.86 (s, OCH3, 3H), 1.62 (d, J = 6.4 Hz, CH3, 3H). ESI-MS m/z: 336.6 and 338.5 [M+H]+.

According to the analysis of related databases, 6602-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tian, Yuanxin; Zhang, Tingting; Long, Lifan; Li, Zhonghuang; Wan, Shanhe; Wang, Guangfa; Yu, Yonghuan; Hou, Ju; Wu, Xiaoyun; Zhang, Jiajie; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 182 – 199;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1196146-82-3 ,Some common heterocyclic compound, 1196146-82-3, molecular formula is C5H3BrClNO, 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.

A solution of 5-bromo-2-chloropyridin-4-ol (200 g 0.960 mol, Intermediate 56) and sodium chlorodifluoroacetate (264 g, 1.73 mol) in DMF (1 L) was added dropwise to a 110-115 C. suspension of Cs2CO3 (469 g, 1.44 mol) in DMF (1 L), and the resulting mixture was stirred at 110-115 C. After the reaction went to completion, mixture was allowed to cool to 50-60 C., and then it was poured into ice water. The resulting mixture was extracted twice with MTBE, and the combined organic layers were washed with water and then concentrated. The concentrate was purified by distillation to afford the title compound as a colorless liquid (bp 75-78 C. at 1-2 mmHg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1196146-82-3, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Wolin, Ronald L.; Fourie, Anne M.; Xue, Xiaohua; (85 pag.)US2019/382350; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 626-60-8, 3-Chloropyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

General procedure: Biaryls 1; General Procedure for the Suzuki-Miyaura Couplingof Aryl ChloridesA stock solution of Pd source (2 mol%) with ligand (correspondingPd/L ratio) in freshly distilled CH2Cl2 (10 mL) was initially preparedwith continuously stirring at r.t. An array of Schlenk tubesequipped with a Teflon-coated magnetic stirrer bar were evacuatedand backfilled with N2 (3 cycles). The stock solution of Pd with ligand(0.5 mL, 0.1 mol% Pd, or please refer to the corresponding Pdloading from different entries) and Et3N (0.1 mL) were transferredto an array of Schlenk tubes via syringes. The diluted Pd complexsolution was stirred and warmed using a household hair drier forabout 1 to 2 min until the solvent started boiling. The solvent wasthen evaporated under high vacuum. Ar2BF3K (0.75 mmol, 1.5equiv) and base (1.5 mmol, 3.0 equiv) were added to an array ofSchlenk tubes. Each tube was carefully evacuated and backfilledwith N2 (3 cycles). Aryl chloride (0.5 mmol, 1.0 equiv) and H2O(1.5 mL) were added via syringe. This batch of Schlenk tube was resealedand magnetically stirred in a preheated 100 C oil bath. Afterthe completion of the reaction, the reaction tubes were allowed toreach r.t. EtOAc (~10 mL) and H2O (~3 mL) were added. The organiclayer was subjected to GC analysis. The filtrate was concentratedunder reduced pressure. The crude products were purified byflash column chromatography on silica gel (230-400 mesh) to affordthe desired product

At the same time, in my other blogs, there are other synthetic methods of this type of compound,626-60-8, 3-Chloropyridine, and friends who are interested can also refer to it.

Reference:
Article; Yuen, On Ying; Wong, Shun Man; Chan, Kin Fai; So, Chau Ming; Kwong, Fuk Yee; Synthesis; vol. 46; 20; (2014); p. 2826 – 2832;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem