Month: July 2021

Application of 15862-46-1, 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.15862-46-1, name is N-(5-Bromopyridin-3-yl)acetamide, molecular formula is C7H7BrN2O, molecular weight is 215.05, as common compound, the synthetic route is as follows.

Intermediate 61 : N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide To a suspension of A/-(5-bromopyridin-3-yl)acetamide (for a preparation see Intermediate 60, 563 mg, 2.62 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1 ,3,2-dioxaborolane) (1330 mg, 5.24 mmol) and potassium acetate (771 mg, 7.85 mmol) in 1 ,4-dioxane (8 mL) in a microwave vial, was added PdC idppf) (192 mg, 0.262 mmol). The vial was sealed and the mixture was heated in a microwave at 100C for 1 h. The mixture was dissolved in ethyl acetate and filtered through a Celite cartridge (10 g). The solvent was evaporated under reduced pressure to give A/-(5-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)pyridin-3-yl)acetamide as a brown oil (1.77 g, 258 %). This crude material was used in the next step without further purification: 100 % conversion assumed therefore maximum purity of crude material is 39 %. LCMS (2 min, High pH): Rt = 0.47 min, MH+ 263

The chemical industry reduces the impact on the environment during synthesis 15862-46-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); 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. 128372-89-4, name is tert-Butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate, molecular formula is C10H15NO3, 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. Safety of tert-Butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate

General procedure: A dried Schlenk flask was charged with arylboronic acid (3, 0.4 mmol), [Rh(L1)(OH)]2 (L1=(S,S)-Ph-thpe, 3.8 mg, 0.005 mmol), KHF2 (3.2 mg, 0.04 mmol), and 1 mL of anhydrous toluene under argon. The resulting mixture was stirred at room temperature for 30 min. 1-N-Boc-2-oxo-5,6-dihydropyridine (2c, 39.4 mg, 0.2 mmol) in toluene (1 mL) was added. Seven minutes later, 0.1 mL of isopropanol was added. After being stirred at room temperature for 2 h, the reaction was quenched with saturated aq NH4Cl, extracted with ethyl acetate (20 mL×3), and the combined organic phases were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel (300-400 mesh) column chromatography to afford 4.

With the rapid development of chemical substances, we look forward to future research findings about 128372-89-4.

Reference:
Article; He, Zhi-Tao; Wei, Ya-Bing; Yu, Hong-Jie; Sun, Cai-Yun; Feng, Chen-Guo; Tian, Ping; Lin, Guo-Qiang; Tetrahedron; vol. 68; 45; (2012); p. 9186 – 9191;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 109-04-6, 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. 109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, 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.

1 ml (10.5 mmol) of 2-bromopyridine in 80 ml of anhydrous THF is cooled to -78 C. under a stream of argon, 9.4 ml (15 mmol) of 1.6N n-BuLi in hexane are added thereto and the mixture is stirred for 30 minutes. 3.2 ml (12 mmol) of tributyltin chloride are thus added and the mixture is stirred, still at -78 C., for 2 hours and afterwards at -20 C. for 3 hours. It is poured into an aqueous NH4Cl solution and extracted with ethyl acetate. The organic phase is dried and the solvent is evaporated. The residue is purified by chromatography on a column of silica gel, elution being carried out with a cyclohexane/ethyl acetate=9/1 mixture, 2.5 g of 2-(tributyltin)pyridine thus being obtained in the form of a yellow oil. 0.31 g of the product thus obtained is dissolved in 5 ml of toluene, and 0.13 ml (0.92 mmol) of 2-(4-bromophenyl)ethanol and 49 mg (0.042 mmol) of tetrakis(triphenylphosphine)Pd are added thereto. The mixture is heated at reflux under a stream of argon for 6 hours. The mixture is poured into water, extraction is carried out with ethyl acetate, the organic phase is dried and the solvent is evaporated. The residue is purified by chromatography on a column of silica gel, elution being carried out with a cyclohexane/ethyl acetate=1/1 and subsequently 4/6 mixture, the title product thus being obtained.

According to the analysis of related databases, 109-04-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Baroni, Marco; Bourrie, Bernard; Casellas, Pierre; Puleo, Letizia; US2005/4132; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73998-95-5, 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. 73998-95-5, name is (4,6-Dichloropyridin-3-yl)methanol, molecular formula is C6H5Cl2NO, 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.

[01368] To a 2000-nt 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed (4,6-dichloropyridin-3-yl)methanol (78.4 g, 440.41 mmol, 1.00 equiv), dichioromethane (1000 mL), PCC (284.83 g, 1.32 mol, 3.00 equiv) and Silica gel (235 g). The resulting mixture was stined at room temperature for 4 h and concentrated under vacuum. The residue was applied onto a silica gel colunm eluted with ethyl acetate/petroleum ether (0:1-1:6) to afford 62 g (80%) of 4,6-dichloropyridine-3-carbaldehyde as a white solid.

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 73998-95-5, (4,6-Dichloropyridin-3-yl)methanol.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16665-38-6, 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. 16665-38-6, name is (4-Methoxypyridin-2-yl)methanol, molecular formula is C7H9NO2, 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 cooled (0 C) solution of 17 (700 mg, 5.03 mmol) in dry CH2Cl2 (4 mL) was added dropwise SOCl2 (2.2 mL, 30.8 mmol). The reaction mixture was stirred at 45 C for 3.5 hr. After removal of the solvent under reduced pressure, the residue was dissolved in sat. NaHCO3 and extracted with CHCl3. The extracts were dried over MgSO4 and concentrated under reduced pressure to give 19 (796 mg, quant.) as a red liquid.

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 16665-38-6, (4-Methoxypyridin-2-yl)methanol.

Reference:
Article; Fuchida, Hirokazu; Tabata, Shigekazu; Shindo, Naoya; Takashima, Ippei; Leng, Qiao; Hatsuyama, Yuji; Hamachi, Itaru; Ojida, Akio; Bulletin of the Chemical Society of Japan; vol. 88; 6; (2015); p. 784 – 791;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 14667-47-1, 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 14667-47-1 as follows.

2-Amino-nicotinic acid methyl ester (1.00g, 6.57 mmol) described in Preparation Example A-2 was dissolved at 0C in a mixed solution of nitric acid (0.7mL) and sulfuric acid (2.6mL), which was stirred at 0C for 40 minute and at room temperature for 19 hours, then, further stirred at 70C for 4 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution at 0C, which was extracted with ethyl acetate and tetrahydrofuran, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. Methanol was added to the residue, the precipitated solid was filtered to obtain the title compound (459mg, 2.33mmol, 35%) as a white solid. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 3.86 (3H, s), 8.14 (1H, brs), 8.62 (1H, brs), 8.68 (1 H, d, J=2.7Hz), 9.04 (1 H, d, J=2.9Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14667-47-1, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14150-94-8 , The common heterocyclic compound, 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one, molecular formula is C6H5N3O5, 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 SP-0010418-2 (1.2 g, 5.128 mmol), 1-methyl-3,5-dinitropyridin- 2(1H)-one (1.53 g, 7.692 mmol) and 7.0 M NH3/MeOH (2.0 mL) in MeOH (8.0 mL) was stirred at 90 C for 0.5 h under microwave irridation. The residue was purified by silica gel column chromatography (using petroleum ether/EtOAc = 10:0 – 7:3) to give mixture SP0010418-162-3A and SP-0010418-162-3B (910 mg, yield: 57%). LC-MS 314 (M+H), 91%(UV2l4nm).

The synthetic route of 14150-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; F.HOFFMANN-LAROCHE LTD; YUAN, Junying; HAN, Nianhe; YI, Hua; WANG, Yuguang; YANG, Song; WONG, Jason, Christopher; WO2014/145512; (2014); A2;,
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. 15513-52-7, name is 2,6-Dimethyl-3-nitropyridine, molecular formula is C7H8N2O2, 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. Quality Control of 2,6-Dimethyl-3-nitropyridine

3-Nitro-2,6-lutidine (2.50 g, 16.5 mmol, 1 equiv.) was dissolved in 200 mL of argonpurged carbon tetrachloride. The reaction mixture was heated to 50 C under argon. AIBN (0.14 g, 0.83 mmol, 5 mol%) was added to the reaction mixture in one portion under constant stirring, followed by the addition of NBS (2.93 g, 16.5 mmol, 1 equiv.) in small portions over a period of 2 hours. The reaction mixture was further refluxed for 8 hours at constant stirring and under light irradiation. Once the reaction was complete, solvent was removed in vacuo producing a brownish residue. This residue was suspended in a mixture of methanol-dichloromethane, in which non-dissolved solids were removed by filtering through a Si02 plug (ca. 120 mL) using an eluent of methanol-dichloromethane (1:20 v/v). Fractions containing ii were combined and solvent was removed in vacuo. The resultant oil was subject to Si02 column chromatography using a mixture of ethyl acetate (gradient from 2% to 10%) in hexanes as an eluent. Fractions containing product were concentrated in vacuo producinganalytically pure ii. Yield: 0.41 g, 1.78 mmol, 11%. ?H NMR, 500 MHz (CDC13, ppm): oe =8.26 d (1H, Ar, J = 9 Hz), 7.47 d (1H, Ar, J = 9 Hz), 4.52 s (2H, CH2), 2.83 s (3H, CH3). ?3C NMR, 75 MHz (CDC13, ppm): oe = 160.46, 153.73, 144.66, 133.66, 121.61, 32.07, 23.84. ESIMS (mlz): [M+H], calculated: 231.0, found: 231.0.

With the rapid development of chemical substances, we look forward to future research findings about 15513-52-7.

Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK UNIVERSITY AT BUFFALO; HEALTH RESEARCH, INC.; MORROW, Janet, R.; TSITOVICH, Pavel, B.; DORAZIO, Sarina, J.; OLATUNDE, Abiola, O.; SNYDER, Eric, M.; SPERNYAK, Joseph, A.; BURNS, Patrick; BOND, Christopher, J.; WO2015/38943; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1195-59-1 , The common heterocyclic compound, 1195-59-1, name is 2,6-Pyridinedimethanol, molecular formula is C7H9NO2, 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.

Example A Preparation of 2,6-bis(chloromethyl)pyridine To 100 mL of thionyl chloride that was cooled (ice bath) was added 24 g (0.17 mol) of 2,6-bis(hydroxymethyl)pyridine. After 30 min, the reaction mixture was warmed to room temperature, then refluxed for 1.5 hrs. After cooling the reaction mixture to room temperature, the solid which formed was filtered, washed with benzene and dried in vacuo. The solid was then neutralized with saturated NaHCO3, filtered and dried to yield 23.1 g (71.5%) of the titled product as an off-white crystalline solid, mp 74.5-75.5 C., and further characterized by: 1 H NMR (CDCl3); delta 4.88 (s, 4H), 7.25-7.95 (m, 3H).

The synthetic route of 1195-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; The University of Texas; US5834456; (1998); A;,
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.139042-59-4, name is 5-Acetyl-2-bromopyridine, molecular formula is C7H6BrNO, molecular weight is 200.03, as common compound, the synthetic route is as follows.COA of Formula: C7H6BrNO

In a 50 mL round-bottomed flask under nitrogen, sodium borohydride (0.390 g, 10.31 mmol) was added portionwise on 5 min to a solution of 5-acetyl-2-bromopyridine (0.515 g, 2.57 mmol) in 2-propanol (10 mL) and water (4 mL) and the mixture was stirred at room temperature for 30 min. The mixture was then concentrated in vacuo and water was added to the concentrate. The mixture was extracted with ethyl acetate (x3) and the combined organic extract was dried over anhydrous Na2SO4 and concentrated. The obtained residue was purified on the ISCO using a 25g SILICYCLE column (elution with hexanes-EtOAc) to give the title material (0.470 g, 90%) as colorless oil. LC (Method B): 1.233 min. LCMS (APCI): calcd for C7H9BrNO [M+H]+ m/z 201.986, found 202.0. 1H NMR (400 MHz, acetone-d6): delta ppm 8.38 (d, J= 2.7 Hz, 1H) 7.71 – 7.77 (m, 1H) 7.54 (d, J= 8.2 Hz, 1H) 4.92 (q, J= 6.7 Hz, 1H) 1.43 (d, J= 6.7 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139042-59-4, 5-Acetyl-2-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; PRIESTLEY, Eldon Scott; POSY, Shoshana L.; TREMBLAY, Francois Tremblay; MARTEL, Alain; MARINIER, Anne; WO2013/163241; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem