Day: April 20, 2022

Synthetic Route of 40473-07-2 , The common heterocyclic compound, 40473-07-2, name is 2-Bromo-6-methoxypyridine, molecular formula is C6H6BrNO, 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.

Preparation 21 : 2-methoxy-6-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)- nicotinamide; Step 1 : theta-bromo^-methoxy-nicotinic acid; A solution of 2,2,6,6-tetramethylpiperidine (0.766 g, 5.32 mmol) in tetrahydrofuran (5 mL) was cooled to -78C under nitrogen. 2.5M n-butyllithium in hexanes (2.34 ml_, 0.375 g, 5.85 mmol) and the mixture was stirred at -780C for 30 min. To the reaction mixture was added a solution of 2-bromo-6-methoxypridine (1.00 g, 5.32mmol) in tetrahydrofuran (5 mL) dropwise. The reaction was stirred at -78C for 1 h. After this time, an excess of dry ice was added to the reaction mixture and the reaction was allowed to warm to room temperature for 3 h. To the mixture was added water and ethyl acetate, the layers were separated. The aqueous layer was acidified to pH 4. The aqueous layer was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to an off-white solid (0.530 g, 42.9 %) 1 H NMR (500 MHz, DMSO-d6) delta ppm 2.52 (2 H, br. s.), 3.32 (1 H, br. s.), 3.92 (1 H, m), 3.90 (1 H, d, J=2.9 Hz), 8.03 (1 H, d, J=7.8 Hz).

The synthetic route of 40473-07-2 has been constantly updated, and we look forward to future research findings.

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

Electric Literature of 179687-79-7, 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 179687-79-7 as follows.

2-(2-Chloro-4-nitro-phenoxymethyl)-pyridine (8 g, 30.2 mmol, 1 equiv) and 8.44 g iron (151.1 mmol, 5 equiv) in 100 mL acetic acid and 50 mL EtOAc were stirred at rt overnight. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo and neutralized with saturated Na2CO3 solution. The solution was EPO extracted with EtOAc and the organic layer was washed with brine and concentrated in vacuo. The resulting crude material was purified by flash chromatography eluting with EtOAc/hexane (3:7) to give 3-chloro-4-(pyridin-2-ylmethoxy)-phenylamine (3.2 g, 52%) as a white solid. 1H-NMR (CDCl3) delta 5.18 (s, 2H), 6.50 (dd, IH)5 6.76 (d, IH),. 6.80 (d, IH), 7.22 (m, IH), 7.64 (d, IH), 7.73 (td, IH), 8.55 (m, IH); LCMS RT = 0.89 min; [M+H]+ = 235.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,179687-79-7, its application will become more common.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/55268; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59020-10-9, 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. 59020-10-9, name is 3-(Tributylstannyl)pyridine, molecular formula is C17H31NSn, 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.

A stirred solution of 2-bromo-5-nitrobenzotrifuoride (Lancaster Synthesis, GmbH; 3.37 g, 12.5 [MMOL)] and [3- (TRI-N-BUTYLSTANNYL)] pyridine (Maybridge Chemical Co. Ltd. , England; 5.0 g, 13.6 [MMOL)] in xylene (75 mL) was purged with argon for 10 minutes at [20C.] Tetrakis (triphenylphosphine) palladium (0) (1.4 g, 1.25 [MMOL)] is then added and the resulting mixture is heated at [130C] for 24 hours under an argon atmosphere. The mixture is then cooled, treated with an aqueous solution of sodium hydroxide (150 mL of 0.1 M) and purged with air for 2 hours. The resulting mixture is then diluted with ethylacetate (200 mL) and filtered. The orgainic phase is then sequentially washed with water (2 x 80 mL) and saturated aqueous sodium chloride (1 x 80 mL), dried [(MGS04),] filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography (silica gel, eluent 50% ethyl acetate in hexane) to afford [3- [ (4-NITRO-3- (TRIFLUOROMETHYL) PHENYL]] pyridine. This product is dissolved in ethanol (200 mL) and hydrogenated at atmospheric pressure over Raney nickel (0.23 g) at [22C.] The calculated amount of hydrogen is taken up in 24 hours. The mixture is then filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by chromatography (silica gel ; eluent 50% ethyl acetate in hexane) and recrystallised from ether-hexane to give the title compound as a colourless crystalline solid, m. p. [92-93C.]

According to the analysis of related databases, 59020-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/5281; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16744-81-3, 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 16744-81-3, name is 4-Methoxypicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The E isomer of hydrazones 1-15 all can be easily to get by similar procedures. The corresponding aldehydes and hydrazine hydrochloride were added to the methanol solution, then the reaction mixture was heated under reflux for 10 h. After the reaction was finished, removed the solvent in vacuo. The residue was dissolved in water and neutralized with saturated NaHCO3 solution. Afterwards, extracted with dichloromethane and collected the organic layer. The organic layer were dried over by Na2SO4, filtered and concentrated. The residue was recrystallized by methanol to give the pure product.

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 16744-81-3, 4-Methoxypicolinaldehyde.

Reference:
Article; Lu, Chaocao; Htan, Bu; Fu, Shitao; Ma, Chunmiao; Gan, Quan; Tetrahedron; vol. 75; 30; (2019); p. 4010 – 4016;,
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.28733-43-9, name is 5-Bromonicotinamide, molecular formula is C6H5BrN2O, molecular weight is 201.02, as common compound, the synthetic route is as follows.name: 5-Bromonicotinamide

Example 23B 3-amino-5-bromopyridine A solution of 3M NaOH (250 mL) at room temperature was treated with bromine (25.9 g, 162 mmol), stirred for 15 minutes, treated with 5-bromonicotinamide (25 g, 124 mmol), stirred for 45 minutes, heated to 85-100 C. for 3 hours, cooled to room temperature, adjusted to pH 1 with 10% HCl (aq.) washed twice with diethyl ether. The aqueous layer was adjusted to pH~10-11 with solid NaOH, and extracted four times with diethyl ether and twice with dichloromethane. The combined extracts were dried (MgSO4), filtered, and concentrated to provide the desired product (13.3 g, 62%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,28733-43-9, 5-Bromonicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 120739-77-7 ,Some common heterocyclic compound, 120739-77-7, molecular formula is C8H11ClN2, 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.

(2): Synthesis of N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1-(methylthio)-2- nitroethenamine To a 100 ml three necked round bottom flask was added N-((6-chloropyridin-3-yl)methyl)ethanamine (17.0 g, 0.1 mol), (2-nitroethene-1,1-diyl)bis(methylsulfane) (15.0 g, 0.09 mol), dry ethanol (50 mL). The mixture was refluxed. After completion, the reaction mixture was cooled to r.t. and concentrated under reduced pressure to obtain crude product as oil, which was purified by column chromatography to afford 5.3 g N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1- (methylthio)-2-nitroethenamine in 18.5% yield. GC-MS: m/z (%)=242 ([M]+-46, 53), 227 (15), 213 (100), 169 (45), 155 (28), 141 (29), 126 (91), 90 (12).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,120739-77-7, its application will become more common.

Reference:
Patent; SHANGHAI SHENGNONG PESTICIDE CO., LTD.; EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY; US2011/269751; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23056-47-5 ,Some common heterocyclic compound, 23056-47-5, molecular formula is C6H5BrN2O2, 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.

25.0 g (115.2 mM) of 2-bromo-4-methyl-5-nitropyridine, 44.3 g (230 mM) of methyl fluorosulfonyldifluoroacetate and 17.6 g (92.2 mM) of CuI were suspended in 250 mL of DMF. This reaction mixture was stirred at 120 C. for 48 hours. The medium was cooled and then diluted with 1000 mL of saturated ammonium chloride solution and 100 mL of ammonium hydroxide, and then stirred until homogenized. The product was extracted three times with ethyl acetate. The residue was purified by chromatography on silica gel, using 95/5 and then 90/10 (v/v) cyclohexane/ethyl acetate as eluent. The fractions containing the expected product were combined and concentrated under reduced pressure. The title product was obtained in the form of a brown oil (8.0 g, yield=34%).1H NMR (300 MHz, DMSO) delta=9.29 (s, 1H), 8.21 (s, 1H), 2.68 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23056-47-5, its application will become more common.

Reference:
Patent; Laboratoires Fournier SA; US2012/302560; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 38186-82-2, 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 38186-82-2 as follows.

6-Chloro-5-methylpyridin-3-amine (50 g, 0.352 mol, 1.0 eq) was dissolved in 6 mol/LIn a hydrochloric acid solution (500 mL), stir for 30 minutes, and cool to 0 C.A solution of sodium nitrite (29.1 g, 0.422 mol, 1.2 eq) in water (300 mL) was added dropwise.After the dropwise addition, the mixture was kept for 20 minutes, and returned to room temperature and stirred for 20 minutes.Then heated to 90 C for 30 minutes, LC-MS detection reaction is complete,The system was cooled to room temperature, extracted with EA (500 mL×5), and the organic phases were combined.It is dried, concentrated, and purified by silica gel column chromatography (100-200 mesh silica gel,PE: EA=15:1)The product was obtained as a white solid (17 g, yield: 34%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,38186-82-2, its application will become more common.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; (67 pag.)CN109810041; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 228410-90-0, name is 5-bromo-2-hydroxy-3-nitro-4-picoline. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step 1. 5-Bromo-1,4-dimethyl-3-nitropyridin-2(1H)-one A solution of 5-bromo-4-methyl-3-nitropyridin-2-ol (15.00 g, 64.37 mmol) [Combi-Blocks, AN-1086] in N,N-dimethylformamide (250 mL) was treated with sodium hydride (3.09 g, 77.3 mmol) (60% dispersion on mineral oil) slowly and portionwise, and stirred at RT for 30 min. The reaction mixture was treated with methyl iodide (4.81 mL, 77.2 mmol) dropwise and stirred at RT for 3 h. LCMS indicated a clean peak for methylated product. The reaction mixture was poured over water/ice (?400 mL) and allowed to stir while the ice melted. The aqueous mixture was extracted with ethyl acetate. The organic layer was washed with water (3*) and brine, dried with magnesium sulfate, filtered, and concentrated to give the desired product (14.9 g, 93%) that was used without further purification. LCMS calculated for C7H8BrN2O3 (M+H)+: m/z=247.0, 249.0. found: 247.0, 248.9.

With the rapid development of chemical substances, we look forward to future research findings about 228410-90-0.

Reference:
Patent; INCYTE CORPORATION; Yue, Eddy W.; Combs, Andrew P.; Douty, Brent; US2015/148342; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 87674-15-5, 1-(3-Fluoropyridin-4-yl)ethanol, 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, Product Details of 87674-15-5, blongs to pyridine-derivatives compound. Product Details of 87674-15-5

A mixture of 1-(3-fluoropyridin-4-yl)ethanol (10 g, 70.3 mmol) and commercial activated MnO2 (8 g, 92.1 mmol) in toluene (100 mL) were refluxed until disappearance of starting material. After cooling, the mixture was filtered on a bed of celite, the cake washed with toluene and the organic phases concentrated to give 3-fluoro-4-acetyl pyridine (6.9 g, 70%) that was used directly in the next step.

The synthetic route of 87674-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142415; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem