Month: March 2022

Electric Literature of 1235036-15-3 ,Some common heterocyclic compound, 1235036-15-3, molecular formula is C10H11BrClNO2, 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 Example 1.23.2 (12.3 g) and tert-butyl 3-bromo-6-chloropicolinate (5.9 g) in dioxane (50 mL) was added (1S,3R,5R,7S)-1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (CyTop) (0.52 g) and bis(dibenzylideneacetone)palladium(0) (0.66 g). After several house vacuum/nitrogen refills, potassium phosphate (4.06 g) and water (25 mL) were added and the reaction was heated at 80 C. under nitrogen for 30 minutes. The reaction was cooled and then water and ethyl acetate were added. The organic layer was separated and washed with brine. The combined aqueous layers were extracted with ethyl acetate, and dried over sodium sulfate. The solution was filtered, concentrated and chromatographed on silica gel using 33% ethyl acetate in heptanes to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1235036-15-3, its application will become more common.

Reference:
Patent; AbbVie Inc.; Ackler, Scott L.; Bennett, Nathan B.; Boghaert, Erwin R.; Cullen, Steve C.; Doherty, George; Frey, Robin R.; Haight, Anthony R.; Judd, Andrew S.; Kunzer, Aaron R.; Shen, Xiaoqiang; Song, Xiaohong; Souers, Andrew J.; Sullivan, Gerard M.; Tao, Zhi-Fu; Wang, Xilu; Welch, Dennie S.; Wendt, Michael D.; (210 pag.)US2016/158377; (2016); 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. 17117-13-4, name is 2-Bromo-4-ethoxypyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C7H8BrNO

7.05.01. 2-(3,5-Bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-(4-(4-ethoxy-pyridin-2-yl)-piperazin-1-yl)-ethanone 17 mg BINAP and 24 mg tris-(dibenzylidenacetone)palladium(0) were added to 255 mg casiumcarbonate, 65 mg 2-brom-4-ethoxy-pyridine and 100 mg 2-(3,5-Bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-piperazin-1-yl-ethanone in 10 mL toluole under nitrogen atmosphere. The reaction was refluxed for 4 days. The mixture was filtered and the filtrate was evaporated. The residue was purified by HPLC. Rt: 1.22 min (method B), (M+H)+: 505 By using the same synthesis strategy as for 2-(3,5-Bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-(4-(4-ethoxy-pyridin-2-yl)-piperazin-1-yl)-ethanone the following compounds was obtained:

The synthetic route of 17117-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; US2013/184248; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 562825-95-0, 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.562825-95-0, name is N-Ethyl-3-nitropyridin-4-amine, molecular formula is C7H9N3O2, molecular weight is 167.17, as common compound, the synthetic route is as follows.

A mixture of ethyl (3-nitropyridin-4-yl) amine (11.8 g, 70.0 MMOL), acetic acid (140 mL), sodium acetate (28.7 g, 0.35 mol) and bromine (13.4 g, 84.0 MMOL) was stirred in a pressure vessel at 100 C for 18 h. The solvent was removed in vacuo and the residue partitioned between CH2CI2 and water. The aqueous layer was made basic (PH-8) with NAHCO3 and further extracted with CH2CI2. The combined organic extracts were washed with water, brine and dried (NA2SO4). The solvent was removed in vacuo. and the residue subjected to flash chromatography (20% EtOAc/hexanes, silica gel) to give 10.4 g (60%) of the desired compound. MS (ES+) m/z 246 (M+H) +.

The chemical industry reduces the impact on the environment during synthesis 562825-95-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/11700; (2005); 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. 1192813-41-4, name is 2-(Difluoromethoxy)-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-(Difluoromethoxy)-5-nitropyridine

Step B: 2-Difluoromethoxy-5-nitro-pyridine obtained in Step A (1.6 g) was treated with iron (5 g) and concentrated hydrochloric acid (0.23 ml) in ethanol (15 ml) and water (2.5 ml) at 800C for 20 minutes. Filtration over Celite and evaporation of the solvent afforded 6- difluoromethoxy-pyridin-3-yl-amine (1.4 g) as an orange solid. IH NMR (400 MHz, CDCl3) 3.51 (br s, 2H), 6.89 (d, IH), 7.23 (d, IH), 7.44 (dd, IH), 7.80 (d, IH).

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, 1192813-41-4, 2-(Difluoromethoxy)-5-nitropyridine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CASSAYRE, Jerome Yves; PITTERNA, Thomas; CORSI, Camilla; MAIENFISCH, Peter; WO2011/3684; (2011); 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. 2510-23-8, name is 3-Ethynylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H5N

General procedure: The terminal alkyne (1.0 mmol) was added to a mixtureof HSi(OEt)2Me (5.0 mmol) and KOtBu (1.5 mmol) in a10 mL Schlenk tube with a magnetic stirrer. The Schlenktube was evacuated and back-filled with CO2 for 3 times.After a CO2 ballon was connected, the reactor was moved toa water bath of 40 C. After being stirred for 2 h, the reactionmixture was diluted with water (30 mL), and was extractedwith CH2Cl2 (3×10 mL). The aqueous layer was acidifiedwith aqueous HCl (6 M) and then extracted with diethylether (5×20 mL). The combined organic extracts were driedover Na2SO4 and concentrated under vacuum to give the purepropiolic acid (such as compound 3-phenylpropiolic acid(3a): 98%).

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, 2510-23-8, 3-Ethynylpyridine.

Reference:
Article; Yu, Bo; Yang, Peng; Gao, Xiang; Yang, Zhenzhen; Zhao, Yanfei; Zhang, Hongye; Liu, Zhimin; Science China Chemistry; vol. 61; 4; (2018); p. 449 – 456;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 932702-11-9, 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 932702-11-9 as follows.

Under an argon atmosphere, thionyl chloride (241 mg, 147 41) was added to a solution of iNpyrazolo[4,3-c]pyridine-3-carboxylic acid (300 mg, CAS: 932702-11-9) in ethanol (20 mL). The mixture was then heated to reflux and was allowed to stir for 2 hours. The mixture was cooled to room temperature and was quenched with sat. Na2CO3 solution. The aqueous layer was extracted twice with ethyl acetate (80 mL). The organic layers were washed once with brine, dried overNa2SO4, filtered, evaporated and dried at high vacuum to provide the title compound as a light yellow powder (228 mg, 62%). MS (mlz): 192.1 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,932702-11-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 38923-08-9, Adding some certain compound to certain chemical reactions, such as: 38923-08-9, name is Ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate,molecular formula is C10H9N3O4, 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 38923-08-9.

A suspension of ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate (20) (20 g, 85 mmol) in MeOH (200 ml) was cooled to 0 C, 12M hydrogen chloride (70 ml, 850 mmol) was added drop wise followed by portion wise addition of zinc (22.3 g, 340 mmol). The reaction mixture was stirred for 30 minutes.Next, MeOH (140 ml) was added and the reaction was quenched with concentrated NH3(15 equiv.) and filtered. The solid residue was washed with MeOH (2 x 25 ml). The filtratewas concentrated and re-suspended in CHC13 (700 ml), H20 (300 ml) and concentrated NH3(300 ml, 35% solution). This mixture was stirred until everything was dissolved. The layerswere separated and the water layer was extracted once with CHC13. The organic layers werecombined, washed with a saturated aqueous NaC1 solution (50 ml), dried over MgSO4,filtered and concentrated in vacuo to yield ethyl 6-aminoimidazo [1 ,2-a]pyridine-2-carboxylate (21) (11.8 g, 68%) as a grey/green solid. UPLC-MS confirmed that the desired product was obtained.

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. 38923-08-9, Ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNTHON BIOPHARMACEUTICALS B.V.; HUIJBRGTS, Tijl; ELGERSMA, Ronald Christiaan; BEUSKER, Patrick Henry; JOOSTEN, Johannes Albertus Frederikus; COUMANS, Rudy Gerardus Elisabeth; SPIJKER, Henri Johannes; MENGE, Wiro; DE GROOT, Franciscus Mariuns Hendrikus; WO2015/185142; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 116855-08-4, 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.116855-08-4, name is 1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid, molecular formula is C7H5N3O2, molecular weight is 163.13, as common compound, the synthetic route is as follows.

Step 5[00179] To a solution of lH-pyrazole[3,4-£]pyridine-3-carboxylic acid (V) (0.39 g, 2.4 mmol) in dry MeOH (10 mL) was added concentrated H2S04 (4 drops) and refluxed for 6 h under nitrogen. The solution was cooled and the solvent was evaporated under vacuum. The residue was partitioned between DCM and saturated NaHC03 solution. The organic layer was separated, dried over MgS04, filtered and concentrated under reduced pressure. The crude product was purified on a flash silica gel column (100% DCM?100:3 DCM:MeOH) to produce methyl lH-pyrazolo[3,4-6]pyridine-3- carboxylate (VI) as a white solid (382 mg, 2.16 mmol, 90% yield). 1H NMR (CDC13) delta ppm 4.08 (s, 3 H), 7.38 (m, 1 H), 8.63 (dd, J=8.10, 1.51 Hz, 1 H), 8.72 (dd, J=4.62, 1.41 Hz, 1 H); ESIMS found for C8H7N302 mlz 178.2 (M+H).

Statistics shows that 116855-08-4 is playing an increasingly important role. we look forward to future research findings about 1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid.

Reference:
Patent; EPITHERIX, LLC; HOOD, John; KC, Sunil Kumar; WALLACE, David Mark; WO2011/84486; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866807-27-4, 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. 866807-27-4, name is 3-Amino-6-chloropyridine-2-carboxylic acid, molecular formula is C6H5ClN2O2, 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.

3-amino-6-chloro-pyridine-2-carboxylic acid (95 mg, 0.55 mmol) is taken up in THF (1 mL) and combined with BH3-THF complex (2.2 mL, 2.2mmol, 1 M in THF). The reaction mixture is stirred for 2 d at 200C. The reaction is ended with dilute HCl and H2O, then neutralised with NaHCO3, extracted with EtOAc, the organic phase is dried on MgSO4, the solvent is eliminated in vacuo and (3-amino-6-chloro-pyridin-2-yl)-methanol is obtained (HPLC-MS: tRet. = 0.79 min, MS(M+H)+ = 159; method AFEC).

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 866807-27-4, 3-Amino-6-chloropyridine-2-carboxylic acid.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; BOEHMELT, Guido; KOFINK, Christiane; KUHN, Daniel; MCCONNELL, Darryl; STADTMUELLER, Heinz; WO2010/7116; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1142197-14-5, 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.1142197-14-5, name is 2-Bromo-5-cyclopropylpyridine, molecular formula is C8H8BrN, molecular weight is 198.06, as common compound, the synthetic route is as follows.

To a stirred solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (125 mg, 0.54 mmole) in 8 mL of CH2Cl2, was added 1-methyl imidazole (0.11 mL, 2.5 equiv.) at 0-5 C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-5 C. and then added methane sulfonyl chloride (0.05 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-50 C. Then 6-methylpyridin-2-amine (58 mg, 1 equiv) was added, and stirred for 18h at room temperature. Water (15 mL) was added to the reaction mixture, layers were separated and aqueous layer was extracted with DCM (3×15 mL). The combined organic layer was washed with 1N HCl (15 mL), followed by Sat NaHCO3 (15 mL) and then with brine (10 mL). Combined organic layer was dried over Na2SO4, concentrated and purified by ISCO (silica gel, eluted by 5% MeOH in DCM gradient) to obtained 171 mg (99%) of titled compound as a clear oil.

Statistics shows that 1142197-14-5 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-5-cyclopropylpyridine.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem