Pyridine-derivatives

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

Synthetic Route of 6000-50-6, 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 6000-50-6, name is 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-(4-aminophenyl)-4-{1-[(4-methylphenyl)sulfonyl]-1H-indol-5-yl}pyridazin- 3(2H)-one (200 mg, 0.438 mmol) in dichloromethane (16.2 mL) and N,N-dimethylformamide (4.00 mL) was added pyridine (71.0 muL, 0.876 mmol) followed by portion wise addition of 4- nitrophenyl carbonochloridate (106 mg, 0.526 mmol) over 1 minute, and the reaction mixture stirred at r.t. for1 hour. To this reaction mixture was added N,N-diisopropylethylamine (381 muL, 2.19 mmol) followed by 2,3-dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride (169 mg, 0.876 mmol) under argon and the reaction mixture stirred at r.t. for 16 hours. The reaction mixture was combined with another batch (0.219 mmol), and concentrated to give a residue. The crude residue was triturated with water-ethanol and the resulting precipitate collected by filtration, washed with ethyl acetate, diethyl ether and dried to give 246 mg (90% purity,63% combined yield over two steps) of the desired product as pale yellow solid. (0981) LC-MS (Method 5): Rt = 0.85 min; MS (ESIpos): m/z = 603 [M+H]+ (0982) 1H-NMR (400 MHz, DMSO-D6) delta (ppm): 2.29 (s, 3H), 4.80 (d, 4H), 6.90 (s, 1H), 7.37 (d, 2H), 7.53-7.54 (m, 1H), 7.60-7.66 (m, 2H), 7.83-7.97 (m, 5H), 8.10 (s, 2H), 8.24 (s, 1H), 8.53- 8.55 (m, 1H), 8.63-8.65 (m, 2H).

According to the analysis of related databases, 6000-50-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BOeHNKE, Niels; BERGER, Markus; SOMMER, Anette; HAMMER, Stefanie; FERNANDEZ-MONTALVAN, Ernesto, Amaury; STELTEN-LUDWIG, Beatrix; GUeNTHER, Judith; MAHLERT, Christoph; GREVEN, Simone; SARKER, Abul, Basher; TAIT, Michael; (451 pag.)WO2019/149637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17880-61-4, 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 17880-61-4, name is Methyl 5-ethynylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Sodium 5-[4′-(4′-aminophenyl)buta-1 ‘,3’-diyn-1 -yl]pyridine-2-carboxylate (144): Copper (II) acetate (1 .36 g, 7.46 mmol, 2.0 equiv) is added at room temperature under stream of argon to a stirred solution of 142 (0.60 g, 3.73 mmol) and 4- ethylnylbenzenamine (2.18 g 18.63 mmol, 5.0 equiv) dissolved in anhydrous pyridine (10 mL) and MeOH (10 mL). The reaction mixture is stirred at room temperature for 20 h. The resulting suspension is filtered, and the solid is washed with EtOAc (3^50 mL). The solid is dried under high vacuum for 12 h to afford as an orange powder, and then used for next step directly. 4N NaOH (10 mL) is added to a stirred solution of the crude methyl ester (600 mg) in MeOH (50 mL) at room temperature. Then reaction solution is heated to reflux for 40 min under argon. The reaction mixture turned clear. After all the starting material has been consumed monitored by TLC,the reaction mixture is cooled to room temperature, and the solvents are removed by evaporation under reduced pressure. The yellow solid is washed by water (3^50 mL), EtOAc (3×50 mL) to give a yellow solid (320 mg, 31 % yield, for two steps ), which is used for next step without future purification. 1 H NMR (300 MHz, CD3OD) 56.62 (d, J=8.4 Hz, 2H), 7.26 (d, J=8.7 Hz, 2H), 7.59 (d, J=9.0 Hz, 1 H), 8.27 (d, J=10.2 Hz, 1 H), 9.01 (s, 1 H); 13C NMR (75 MHz, CD3OD) 570.50, 75.996, 78.48, 85.59, 107.59, 1 14.17, 127.44, 133.09, 134.06, 137.62, 142.94, 150.69, 170.58; MS (ESI, positive): m/z 263 [M+H+].

According to the analysis of related databases, 17880-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DUKE UNIVERSITY; ZHOU, Pei; TOONE, Eric, J.; WO2012/31298; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 130658-65-0 ,Some common heterocyclic compound, 130658-65-0, molecular formula is C10H14N2O, 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.

The 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline used as a starting material was prepared as follows:- Diethyl azodicarboxylate (3 ml) was added over 15 minutes to a stirred mixture of 1-(4-pyridyl)piperidin-4-ol (3.39 g), 3-(N-tert-butoxycarbonylamino)phenol (Chemical Abstracts, vol. 119, abstract 139113; PCT Patent Application WO 9306085; 3.98 g), triphenylphosphine (4.99 g) and THF (150 ml) which had been cooled to 4 C. The resultant mixture was stirred for 48 hours at ambient temperature. The solvent was evaporated and the residue was purified by column chromatography using a 9:1 mixture of methylene chloride and methanol as eluent. The resultant foam was crystallized from diethyl ether to give tert-butyl N-{3-[1-(4-pyridyl)piperidin-4-yloxy]phenyl}carbamate (4.65 g), m.p. 165-166 C. A 2.2M solution of hydrogen chloride in methanol (45 ml) was added over 15 minutes to a stirred solution in methanol (25 ml) of a portion (2.53 g) of the carbamate so obtained. The mixture was stirred at ambient temperature for 24 hours. The solvent was evaporated and the residue was dissolved in water (50 ml). A 1M aqueous sodium hydroxide solution (25 ml) was added and the mixture was stirred for 1 hour. The precipitate was collected, washed with water and with diethyl ether and dried. There was thus obtained 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline (1.71 g), m.p. 184-186 C.; NMR Spectrum 1.60 (m, 2H), 1.96 (m, 2H), 3.23 (m, 2H+H2O), 3.65 (m, 2H) 4.48 (m, 1H), 5.00 (s, 2H), 6.16 (m, 3H), 6.82 (d, 2H), 6.88 (t, 1H), 8.15 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,130658-65-0, its application will become more common.

Reference:
Patent; ZENECA LIMITED; US2003/207882; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem