Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine, 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, 727356-19-6, blongs to pyridine-derivatives compound. Safety of 2-Bromo-6-(chloromethyl)pyridine

To a solution of (4-fluorophenyl)-carbamic acid tert-butyl ester (60144-53-8, 750 mg, 3.55 mmol) in tetrahydrofuran (10 ml_) was added sodium hydride (60% dispersion in mineral oil, 150 mg, 3.9 mmol). After 30 minutes, tetra-n-butylammonium iodide (51 mg, 0.36 mmol) and 2-bromo-6-chloromethyl-pyridine (804 mg, 3.9 mmol) was added to the reaction and the mixture was heated to 70C. After 1 hour, the reaction was cooled to room temperature, quenched with saturated sodium bicarbonate (10 mL) and extracted with ethyl acetate (2 x 15 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (silica gel; 10% ethyl acetate in hexanes) provided (6-bromo-pyridin-2-ylmethyl)-(4-fluorophenyl)-carbamic acid terf-butyl ester (700 mg, 1.84 mmol) as an oil which solidified upon standing.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,727356-19-6, its application will become more common.

Reference:
Patent; WYETH; WO2008/73461; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 116308-35-1, Adding some certain compound to certain chemical reactions, such as: 116308-35-1, name is 2-(Trifluoromethyl)nicotinaldehyde,molecular formula is C7H4F3NO, 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 116308-35-1.

A solution of lithium hydroxide (0.8 mg, 0.03 mmol) and 2′-methoxyacetophenone (26 mg, 0.157 mmol) in absolute methanol (1.5 mL) was stirred at room temperature for 15 min. To the resulting mixture was added a solution of 2-(trifluoromethyl)-3-pyridinecarboxaldehyde (6a, 28 mg, 0.16 mmol) in absolute methanol (15 mL). The reaction was stirred overnight at room temperature (approx. 18 h). The reaction was then concentrated on a rotary evaporator and the resulting oily residue purified by chromatography on silica gel using a gradient of 0-100% ethyl acetate in hexane to provide the desired product (17 mg, 35%) as a light yellow waxy solid. 1H NMR (CDCl3): delta 8.71 (d, J = 4.9 Hz, 1H), 8.12 (d, J = 8.1 Hz, 1H), 7.93 (dd, J = 15.8 Hz, 2.0 Hz, 1H), 7.68 (dd, J = 7.6, 1.8 Hz, 1H), 7.56 (dd, J = 8.0, 4.6 Hz, 1H), 7.55 (d, J = 7.4 Hz, 1H), 7.54 (dt, J = 7.4, 1.9 Hz, 1H), 7.36 (d, J = 15,8 Hz, 1H), 7.09 (t, J = 7.6, 1H), 7.03 (d, J = 8.2 Hz, 1H), 3.93 (s, 3H). 13C NMR (CDCl3) delta 190.8, 157.3, 148.2, 147.1, 145.2, 136.5, 135.1, 134.4, 132.6, 131.6, 129.7, 129.6, 127.2, 125.5, 120.0, 110.6, 54.7. HRMS (FAB): calcd C16H12F3NO2 + H = 308.0898, found 308.0889.

According to the analysis of related databases, 116308-35-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lounsbury, Nicole; Mateo, George; Jones, Brielle; Papaiahgari, Srinivas; Thimmulappa, Rajash K.; Teijaro, Christiana; Gordon, John; Korzekwa, Kenneth; Ye, Min; Allaway, Graham; Abou-Gharbia, Magid; Biswal, Shyam; Childers, Wayne; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5352 – 5359;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 883107-62-8, 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. 883107-62-8, name is Methyl 3-amino-2,6-dichloroisonicotinate, molecular formula is C7H6Cl2N2O2, 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.

Step 8: Preparation of 3-amino-2, 6-dichloroisonicotinic acid; 3-Amino-2, 6-dichloroisonicotinic acid methyl ester (460 mg) was dissolved in ethanol (8 mL) , water (2 mL) and potassium hydroxide (234 mg) was added. The solution was stirred for 20 minutes at room temperature and for 1.5 hours under reflux. After cooling to room temperature, 2N hydrochloric acid was added to adjust the pH-value to ~3 and the so- formed yellow precipitate was extracted 3x with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum to afford 420 mg of the title compound of the formulaas a yellow solid. The compound was used in the following reaction step without further purification1H-NMR (CDCl3, TMS) delta (ppm) : 6.21 (2 H, br s), 7.69 (1 H, 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 883107-62-8, Methyl 3-amino-2,6-dichloroisonicotinate.

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

Application of 6515-09-9, 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. 6515-09-9, name is 2,3,6-Trichloropyridine, molecular formula is C5H2Cl3N, 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.

1000mL reaction flask,Added 2,3,6-trichloropyridine 200g,N,N-dimethylethanolamine 300g stirring at room temperature,Add 80% hydrazine hydrate solution 100gAfter the addition,Rising temperature reflux 110 ~ 115 C,After 10 hours of reaction,Sampling HPLC monitoring control raw material (trichloropyridine) Cool to 0 ~ 10 C,Precipitation of solids,filter;Solids are washed with a small amount of water,dry;The product 2-hydrazino-3,6-dichloropyridine ~190g,Yield ~ 97.1% (theory: 195.6g);

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 6515-09-9, 2,3,6-Trichloropyridine.

Reference:
Patent; Shanghai Yaben Chemical Co., Ltd.; Lin Zhigang; Jiang Yueheng; Cai Tong; (5 pag.)CN107778225; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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