Tag: M.W:200-300

Electric Literature of 39856-50-3 ,Some common heterocyclic compound, 39856-50-3, molecular formula is C5H3BrN2O2, 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.

1) 5-Bromo-2-nitropyridine (1 mol, 203 g) was dissolved in 1.5 L of dimethyl sulfoxide, and then an organically modified hectorite-supported ionic liquid material MHIL (40.6 g, 20 wt%) was added. Agitating and dispersing uniformly to obtain a first mixed liquid;2) Piperazine (129.2 g, 1.5 mol) was dissolved in 800 ml of dimethyl sulfoxide to form a piperazine solution, and then the piperazine solution was added dropwise to the first mixture to carry out a condensation reaction at 80 C;3) After 5 hours, the reaction solution was taken for HPLC detection (the percentage of 5-bromo-2-nitropyridine in the reaction solution was 0.08%, and the target product 1-(6-nitropyridin-3-yl)piperazine was 99.68%. Double condensation by-product 0.17%, the balance is unknown impurities), stop the reaction, use an organic microporous membrane with a pore size of 0.5 mum to filter and remove the organic modified hectorite-loaded ionic liquid material to obtain a filtrate;4) The filtrate is warmed to 60-65 C, and then the aqueous solution of methylamine at a concentration of 3 V% is added dropwise. When the turbidity occurs in the system, the dropwise addition is stopped, the mixture is kept warm for 20-30 min, and then the aqueous solution of methylamine having a concentration of 3 V% is continuously added dropwise. The concentration of 1-(6-nitropyridin-3-yl)piperazine in the solution was no longer decreased, and the temperature was naturally lowered to room temperature, filtered, and dried under vacuum at 45 C to obtain 197.4 g of a solid. The yield was 94.8%. 99.92% (external standard method); LC-MS: m/z = 209.1 [M+H].The ionic liquid material supported by the organic modified hectorite filtered by filtration was air-dried by acetone and recovered, and the yield of 1-(6-nitropyridin-3-yl)piperazine was 94.2%, and the content was 99.89%. Compared with the catalytic effect of fresh preparation, the catalytic material prepared by the invention can be recycled and used to reduce the production cost of the condensation step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39856-50-3, its application will become more common.

Reference:
Patent; Zheng Chuanhua; Lu Xueling; Zhang Lei; (10 pag.)CN109369517; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5470-17-7, 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.5470-17-7, name is 3-Bromo-2-chloro-5-nitropyridine, molecular formula is C5H2BrClN2O2, molecular weight is 237.44, as common compound, the synthetic route is as follows.

Example 16: Representative synthesis of Compound 201 Summary Compound 201 was synthesized via a seven-step route depicted below.Scheme: 36Ref: 1) Justus Liebigs Annalen tier Chemie, 1937, 529, 291 Experimental Step 1 To a solution of 3-bromo-2-chloro-5-nitropyridine (23.5g, 100 mmol ) in 200 mL of CH3OH was added CFbONa ( 54g , 1.0 mol ) with stirring in an ice bath. The resulting solution was heated at 80 C for 12 hrs and cooled to room temperature .The reaction mixture was diluted with 200 mL of H20 and extracted with ethyl acetate (3 x 250 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated to give a residue, which was purified by column chromatography over silica gel (50: 1 , petroleum ether/ EtOAc ) to afford a( 6.8 g, 34% ) as a yellow oil.

Statistics shows that 5470-17-7 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-chloro-5-nitropyridine.

Reference:
Patent; GENZYME CORPORATION; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; MAZITSCHEK, Ralph; CLARDY, Jon, C.; WIRTH, Dyann; WIEGAND, Roger; URGAONKAR, Sameer; BANIECKI, Mary, Lynn; CORTESE, Joseph; CELATKA, Cassandra; XIANG, Yibin; SKERLJ, Renato; BOURQUE, Elyse, M.j.; WO2011/53697; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1261269-66-2, Adding some certain compound to certain chemical reactions, such as: 1261269-66-2, name is 2,4,6-Trichloronicotinaldehyde,molecular formula is C6H2Cl3NO, 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 1261269-66-2.

A suspension of 2,4,6-trichloropyridine-3-carbaldehyde (5 g, 23.76 mmol, 1.00 equiv) and hydrazine hydrate (3.6 g, 57.53 mmol, 3.00 equiv, 80%) in ethylene glycol dimethyl ether (25 mL) was stirred for 12 h at 45C. After completion the solution was quenched with water and extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:10) to give the title compound (1 g, 22%) as a lightyellow solid. LC-MS (ES, m/z): 188 [M+H].

According to the analysis of related databases, 1261269-66-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 171178-46-4, 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 171178-46-4, name is 5-((tert-Butoxycarbonyl)amino)-2-chloroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 3: Preparation of 5-amino-2-chloroisonicotinic acid; A suspension of 5- tert-butoxycarbonylamino-2-chloro- isonicotinic acid (2.46 g) in aqueous 2N potassium hydroxide solution (45 mL) was stirred at 90¡ãC for 5 hours, After cooling to room temperature, the solution was acidified by slow addition of 6N hydrochloric acid. The formed precipitate was filtered off, washed with water, MTB-ether and hexane and dried in vacuum to afford 700 mg of the title compound of the formulaas beige solid .1H-NMR ( DMSO-D6) delta (ppm) : 7 . 47 ( IH , s ) , 8 . 02 ( IH, 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 171178-46-4, 5-((tert-Butoxycarbonyl)amino)-2-chloroisonicotinic acid.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 882521-63-3, 7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-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, 882521-63-3, blongs to pyridine-derivatives compound. Safety of 7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

General procedure: To a microwave tube was added [1,2,4]triazolo[1,5-a]pyridin-2-amine 13 (1 equiv), K2CO3 (2.0 equiv), Pd(PPh3)4 (0.056 equiv), and the corresponding boronic acid (1.5 equiv). 5 mL of EtOH:H2O (1:1) was used as solvent, and the microwave conditions employed were 150 C for 30 min. After solvent evaporation, the product was purified by flash chromatography on silica gel using as eluent a gradient of EtOAC (0 – 100%) in n-hexane or MeOH (0 – 10%) in DCM to afford the desired compound 16 (adapted from 4).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,882521-63-3, its application will become more common.

Reference:
Article; Ribeiro, Carlos J.A.; Kankanala, Jayakanth; Xie, Jiashu; Williams, Jessica; Aihara, Hideki; Wang, Zhengqiang; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 257 – 261;,
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. 911434-05-4, name is 5-Bromo-2-methyl-3-nitropyridine, molecular formula is C6H5BrN2O2, 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. Recommanded Product: 5-Bromo-2-methyl-3-nitropyridine

[0005691 To a stirred solution of compound 3(1.73 g, 1 eq) in ethanol (10 mL), iron powder (1.78 g, 4eq), water (10 mL) and ammonium chloride (1.7 g,4eq) were added slowly. The reaction mixture was heated to reflux for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated under reduced pressure. The residue was dissolved in ethyl acetate (100 mL) and washed with brine. The organic extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the title compound 4. LCMS (mlz): 188.90 (M+ 2).

With the rapid development of chemical substances, we look forward to future research findings about 911434-05-4.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 105752-11-2, 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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.

A 10 mL CEM microwave vessel was charged with 3-amino-4-iodopyridine (139 mg, 0.63 mmol, Alfa Aesar), 3,6-dihydro-2H-pyridine-l-A^-boc-4-boronic acid pinacol ester (236 mg, 0.76 mmol, Frontier Scientific Inc.), NaOAc (155 mg, 1.90 mmol) and a stirbar. The vessel was sealed, and transferred into a glove box using a standard antichamber evacuate-refill cycle (3 times). The vessel was charged with A-Phos (45 mg, 0.063 mmol, Sigma-Aldrich), and sealed. The vessel was then transferred to a standard hood, and treated with dioxane (4 mL), and water (0.4 mL). The slurry was sonicated and was then heated in a microwave using a CEM explorer at 120 C for 30 min. The solution was treated with a second aliquat of 3,6-dihydro-2H-pyridine-l-A x>c-4-boronic acid pinacol ester (236 mg, 0.76 mmol, Frontier Scientific Inc.) and was then heated in a microwave using a CEM explorer at 120 C for 30 min The solution was treated with dichlorobis(di-?er?-butylphenylphosphine)palladium(II) (20 mg, 0.032 mmol, Alfa Aesar) and was then heated in a microwave using a CEM explorer at 120 C for 30 min. The solution was cooled to RT overnight under a stream of N2. The residue was treated with dry THF (5 mL) and SiliaMetS TAAcOH (1.29 g, 0.63 mmol, Silicycle). The vessel was crimped with a PTFE lined seal, and heated at 60 C for 3 h. The slurry was N2- pressure filtered through a glass frit (10 mL Bohdan) fitted with a 0.22 muiotaeta PTFE, 25 mm syringe filter unit (Millipore, SLFG025NK). The silica was washed with dry THF (5 x 5 mL), and concentrated in vacuo. The crude material was purified by silica gel chromatography (10% EtOH in DCE) to afford teri-butyl 3′-amino-5,6-dihydro-[4,4′- bipyridine]-l(2H)-carboxylate (77 mg, 0.28 mmol, 44 % yield). MS (ESI, pos. ion) m/z: 276.0 (M+l).

Statistics shows that 105752-11-2 is playing an increasingly important role. we look forward to future research findings about 3-Amino-4-iodopyridine.

Reference:
Patent; AMGEN INC.; D’AMICO, Derin C.; HERBERICH, Bradley J.; JACKSON, Claire L.M.; PETTUS, Liping H.; TASKER, Andrew; WANG, Hui-Ling; WU, Bin; WURZ, Ryan; WO2012/148775; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 926294-07-7 ,Some common heterocyclic compound, 926294-07-7, molecular formula is C7H6BrNO, 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 mixture of 6-bromo-4-methylpyridine-3-carboxaldehyde (1.53 g, 7.69 mmol), 4- hydroxy-benzoic acid methyl ester (1.22 g, 8.0 mmol) and K2CO3 (1.06 g, 7.69 mmol) in DMF (20 mL) was stirred at 125 C for 3 h. The mixture was cooled to room temperature and DMF EPO was removed. Aqueous work-up and purification by flash chromatography on silica gel (CH3OH/CH2C12, 1:50 in v/v) afforded 4-(5-formyl-4-methyl-pyridin-2-yloxy)-benzoic acid methyl ester as a white solid (0.524 g, 25%). 1H NMR (CDCl3) delta 2.68 (s, 3H), 3.92 (s, 3H), 6.84 (s, IH), 7.19-7.26 (m, 2H), 8.10-8.14 (m, 2H), 8.50 (s, IH), 10.11 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,926294-07-7, its application will become more common.

Reference:
Patent; ANORMED INC.; WO2007/22371; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 80194-68-9, Adding some certain compound to certain chemical reactions, such as: 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid,molecular formula is C7H3ClF3NO2, 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 80194-68-9.

To a stirred solution of C-(4-cyclopropylmethanesulfonyl1-1-cyclopropylmethyl-cyclohexyl)-methylamine (64 mg; 0.224 mmol) in DCM (1 ml) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide (100 mg; 0.336 mmol), 1-hydroxybenzotriazole hydrate (5 mg; 0.0336 mmol), and 3-chloro-5-trifluoromethyl)pyridine-2-carboxylic acid (65 mg; 0.288 mmol). The mixture was stirred for 20 hours. Water (5 ml) and DCM (5 ml) were added and the mixture was stirred vigorously for 5 minutes then passed through a PTFE separation frit. The organic phase was collected and evaporated in vacuo. The residue was dissolved in MeOH and passed through a Si-carbonate cartridge, eluding with MeOH. The filtrate was evaporated in vacuo to give an oil. The crude product was purified by prep. TLC eluted with 50% EtOAc in hexane to give a colourless oil. The oil was crystallized from EtOAC using hexane to give a white solid (57 mg). 1H NMR (400 MHz, CDCl3): delta 8.72 (1H, s), 8.07 (1H, s), 7.80 (1H, t, J 6.5), 3.60 (2H, d, J 6.6), 2.94-2.88 (3H, m), 2.09-2.05 (2H, m), 2.00-1.86 (4H, m), 1.41-1.35 (2H, m), 1.26-1.16 (3H, m), 0.78-0.70 (3H, m), 0.56-0.52 (2H, m), 0.44-0.40 (2H, m), 0.09-0.07 (2H, m). MS (m/e)=493.

According to the analysis of related databases, 80194-68-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Blackaby, Wesley Peter; Castro Pineiro, Jose Luis; Lewis, Richard Thomas; Naylor, Elizabeth Mary; Street, Leslie Joseph; US2006/276655; (2006); 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.58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.05, as common compound, the synthetic route is as follows.Application In Synthesis of Ethyl 2,6-dichloronicotinate

Step 2: ethyl 6-chloiO-2-ethoxynicotinate; To a solution of ethyl 2,6-dichloronicotinate (5.0 g, 22.72 mmol) in dichloromethane (25 ml_) at 00C was added sodium ethoxide (2.12 g, 29.5 mmol) slowly. The reaction was stirred at 00C for 3 h and then warmed to ambient temperature over 16 h. The reaction was diluted with dichloromethane (20 ml_) and water (20 ml_) and the layers were separated. The aqueous layer was extracted an additional time with dichloromethane (20 ml_). The organic layers were combined, washed with brine (20 ml_), dried over magnesium sulfate, filtered, and concentrated to give the title compound (4.38 g, 84%) as a light yellow solid. 1 H NMR (400 MHz, DMSO-Cf6) delta ppm 1.22 – 1.40 (m, 6 H) 4.27 (q, J=7.03 Hz, 2 H) 4.37 (q, J=7.03 Hz, 2 H) 7.18 (d, J=8.00 Hz, 1 H) 8.15 (d, J=8.00 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-86-4, Ethyl 2,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem