Tag: M.W:100-200

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

Adding a certain compound to certain chemical reactions, such as: 22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, 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, COA of Formula: C6H5ClN2O2, blongs to pyridine-derivatives compound. COA of Formula: C6H5ClN2O2

To a stirred solution of 55 (5 g, 29 mmol) in EtOH (20 mL) and cone HC1 (20 mL) was added Fe powder (16.2 g, 289 mmole) in small portions at RT over 30 min. The resulting reaction mixture was stirred at RT for an additional 30 min. The solvent was removed in vacuo and water was added to the residue which was then neutralized with NaHC03 and diluted with EtOAc. The reaction mixture was filtered through Celite and washed with EtOAc. The filtrate was transferred to a separatory funnel and the phases separated. The organic layer was washed with water and brine, dried over Na2S0 and concentrated to afford 56 (4.1 g, 99 %) as a yellow solid.

The synthetic route of 22280-60-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; XU, Wei; (170 pag.)WO2017/4609; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1095823-39-4, Adding some certain compound to certain chemical reactions, such as: 1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine,molecular formula is C6H4ClF3N2, 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 1095823-39-4.

Synthesis of Compound A.7. A 20 mL vial was charged with compound A.5 (191.8 mg, 0.0006561 mol), methylene chloride (3.0 mL), a 2.0 M solution of oxalyl chloride in methylene chloride (390 muL) and DMF (10.0 muL, 0.000129 mol). The reaction mixture was stirred for 15 minutes at RT, then concentrated in vacuo and the resultant residue was taken up in acetonitrile (3.0 mL). To this solution was added a solution of compound A.6 (129 mg, 0.000656 mol) and pyridine (0.5 mL, 0.006 mol) in acetonitrile (1.5 mL). The reaction mixture was stirred at RT overnight. The solvent was removed under reduced pressure, and the residue was purified by combiflash (0-30% EtOAc/CH2Cl2) to give compound A.7 in 49% yield. MS: m/z 471 [M+1]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 188577-68-6, 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.188577-68-6, name is 4,5-Dichloropyridin-2-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.

INTERMEDIATE 2 4,5-Dichloro- V-nitropyridine-2-amine 4,5-Dichloropyridin-2-amine (INTERMEDIATE 1, 45.2 g, 283.0 mmol) was added to 270 mL of ice cold cone. H2SO4, in small portions over ca 20 min. When dissolved, cone. HNO3 (22 g) was added dropwise and the mixture was stirred at ca 5 C for 3.5 h. LCMS indicated total conversion to expected product. The cold mixture was poured on crushed ice/water mixture (3 L), stirred for ca 5 min and then filtered. The solid was collected and slurried in ice cold water (500 mL) and filtered. The procedure was repeated until neutral pH. When semi dry on the filter, the solid was dissolved in EtOAc (ca. 3 L) , washed with brine (ca. 100 mL) and the organic layer was dried with Na2S04, filtered, and evaporated to furnish 46.2 g (78%) of 97% pure title product as beige-orange solid. 1H NMR (600 MHz, CD3OD) delta ppm 8.47 (s, 1 H) 8.08 (s, 1 H). MS: (ESI+) m/z 208, 210, 212 [M+H]+, di-chlorine isotopic pattern. INTERMEDIATE 3 4,5-Dichloro-3-nitropyridine-2-amine 4,5-Dichloro-N-nitropyridin-2-amine (INTERMEDIATE 2, 20.0 g, 96.2 mmol) was added to 200 mL of cone. H2S04 at room temperature. After stirring at 40 C for 2.5 h the mixture was cooled to below room temperature and poured onto crushed ice (2 L) while stirring. After the ice had melted, the volume was adjusted to ca. 2 L with ice cold water and the yellow precipitate was collected by filtration and washed with ice cold water until neutral pH (3 x 250 mL). The solid was allowed to semi-dry on the filter and was then dissolved in EtOAc (ca. 800 mL). The organic phase was washed with 0.25 M NaOH (3×30 mL), water (3×15 mL) and brine (15 mL), dried (Na2S04), filtered and the solvent evaporated to furnish 11.7 g (59%) of 99% pure title product as yellow solid. 1H NMR (600 MHz, CD3OD) delta ppm 8.26 (s, 1 H). MS: (ESI+) m/z 208, 210, 212 [M+H]+ chlorine isotopic pattern.

Statistics shows that 188577-68-6 is playing an increasingly important role. we look forward to future research findings about 4,5-Dichloropyridin-2-amine.

Reference:
Patent; KANCERA AB; MELLSTEDT, Hakan; BYSTROeM, Styrbjoern; VAGBERG, Jan; OLSSON, Elisabeth; (274 pag.)WO2016/124553; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 188577-68-6, 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 188577-68-6, name is 4,5-Dichloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of ( 4,5-dichloropyridin-2-amine (0.1 g, 0.61 mmol) in dioxane (5 mL) was added iodobenzene (0.25 g, 1.22 mmol), cesium carbonate (0.597 g, 1.83 mmol), and Xantphos (4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; 0.035 g, 0.06 mmol). The mixture was degassed with argon for 10 min, then tris(dibenzylideneacetone)dipalladium(0) (0.029 g, 0.03 mmol) was added, and the mixture was degassed again with argon for 10 min. The mixture was stirred for 3 h at 100 C. The mixture was cooled, concentrated under reduced pressure, diluted with water (10 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by gradient column chromatography using ethyl acetate in hexane as eluent to afford 4,5-dichloro-N-phenylpyridin-2-amine as an off-white solid (82 mg, 56% yield). 1HNMR (400 MHz, CDCl3): delta 8.17 (s, 1H), 7.36 (t, J=7.2 Hz, 2H), 7.28 (s, 2H), 7.12 (t, J=7.6 Hz, 1H), 6.92 (s, 1H), 6.51 (br s, 1H). LC-MS calcd exact mass 238.01, found m/z 239.1 [M+H]+.

According to the analysis of related databases, 188577-68-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Asana Biosciences, LLC; Venkatesan, Aranapakam M.; Thompson, Scott K.; Smith, Roger A.; Reddy, Sanjeeva P.; (166 pag.)US2016/362407; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine, the common compound, a new synthetic route is introduced below. name: N-((6-Chloropyridin-3-yl)methyl)ethanamine

General procedure: This embodiment is basically the same as Embodiment 1, except that:Step 2, using 170 g (15%) sodium carbonate instead of 52 g (40%) potassium carbonate aqueous solution, 41.8 g (98%) 2-chloro-5-ethylaminomethylpyridine instead of 40% methylamine.As a result, 70.5 g of (E)-N-(2-chloro-5-thiazolylmethyl)-N-ethyl-N’-(6-chloro-3-pyridylmethyl)-N’-ethyl-2- Nitrovinylidene diamine, content 98.1%, yield 83.1%. _: 2 In a 500 mL four-necked flask, 35.1 g (89%) of 1,1-dichloronitroethylene (0.22 mol) and 150 mL of dichloromethane were added.Stirring was carried out to 0 to 10 C, and 36.2 g (98%) of 2-chloro-5-ethylaminomethylthiazole (0.2 mol) was added dropwise. After the addition, 52 g (40%) of potassium carbonate aqueous solution was added dropwise at this temperature. , keep warm for 2 hours,Sampling HPLC analysis of N-(2-chloro-5-thiazole) methyl-N-ethylamine conversion rate of 98% or more, adding 38.8g (40%) methylamine aqueous solution (0.5mol) at 5-10 C, plus Stir for 1 hour after finishing.The temperature was raised to 20 to 25 C for 2 hours, and the oil layer was separated and allowed to stand, and the aqueous layer was extracted with dichloromethane for 3 times.The oil layer was desolvated, and 70 g of ethyl acetate was added to the residue, stirred well, and cooled to 0 to 5 C for filtration.Drying to obtain 50 g of (E)-N-(2-chloro-5-thiazolylmethyl)-N-ethyl-N’-methyl-2-nitrovinylidene diamine, content 98%, yield 88.6% .

The synthetic route of 120739-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lianyungang Liben Crop Technology Co., Ltd.; Wu Hailin; Dong Junjie; Dai Zhanyong; Gong Jian; Li Datie; (6 pag.)CN107474022; (2017); 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.65169-42-8, name is Methyl 6-chloro-5-methylnicotinate, molecular formula is C8H8ClNO2, molecular weight is 185.6076, as common compound, the synthetic route is as follows.Product Details of 65169-42-8

To a suspension of methyl 6-chloro-5-methyl-nicotinate (467 mg) in carbon tetrachloride (25 mL) were added N-bromosuccinimide (1.34 g) and benzoyl peroxide (218 mg), and the mixture was stirred at 100C for 7.5 hours. The mixture was cooled to room temperature, and to the reaction mixture were added saturated aqueous sodium thiosulfate solution and water, and the reaction mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtrated, and then concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (833 mg). LC-MS, condition B ([M+H]+/Rt (min)): 341.9/1.011

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65169-42-8, Methyl 6-chloro-5-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Dainippon Pharma Co., Ltd.; FUKUNAGA, Yuichi; YAMAKAWA, Erina; SUGARU, Eiji; IKEDA, Satoshi; OTSUBO, Tsuguteru; UMEHARA, Hiroki; LI, Chiang Jia; (87 pag.)EP3560494; (2019); 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.695-98-7, name is 2,3,5-Trimethylpyridine, molecular formula is C8H11N, molecular weight is 121.1796, as common compound, the synthetic route is as follows.SDS of cas: 695-98-7

In dichloromethane (15.0 ml), 2,3,5-trimethyl-pyridine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (1.29 g) was dissolved. After having been cooled to 0 C, the reaction solution was added with m-chloroperbenzoic acid (2.53 g), followed by stirring at room temperature for 1.5 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. Subsequently, the organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the resultant residue in dichloromethane (25.0 ml) . The reaction solution was added with trifluoroacetic anhydride (2.8 ml) and the whole was refluxed under heating for 3.5 hours. After the reaction solution was cooled to room temperature, the solvent was distilled off. The resultant residue was dissolved in methanol (60.0 ml). After having been cooled to 0C, the reaction solution was added with a 12.5% sodiummethoxide/methanol solution to adj ust the solution to pH 10, and the whole was stirred at room temperature for 16.5 hours. After the solvent was distilled off, the residue was added with distilled water and subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the residue in chloroform (30.0 ml). The reaction solution was added with manganese dioxide (chemically processed product) (6.10 g) and then stirred at room temperature for 18 hours. The reaction solution was filtrated through Celite. The solvent in the filtrate was distilled off and the resultant residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.14 g) as a yellow oily substance. MS(FAB,Pos.):m/z=136[M+H]+ 1H-NMR(500MHz,CDCl3):delta=2.40(3H,s), 2.63(3H,s), 7.43(1H,brs), 8.48(1H,brs),10.16(1H,s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,695-98-7, 2,3,5-Trimethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 51269-82-0, Adding some certain compound to certain chemical reactions, such as: 51269-82-0, name is 5-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 51269-82-0.

A mixture of 5-chloro-nicotinonitrile (63.8 mg, 461 mumol), 2-propanol (9.2 mL; not dry), and CaSO4 (-325 mesh) (920 mg, 6.76 mmol) was treated with a suspension of Raney Cobalt 2700 in 2-propanol under air (2 mL) (prepared by diluting 2 mL of the commercial water slurry with 15 mL 2-propanol, centrifuging, decanting, and repeating with 2×15 mL 2-propanol, then resuspending with 2 mL 2-propanol). The flask was then sealed and evacuated until bubbles formed, and the evacuated flask was flushed with H2 gas via balloon pressure. After 11 h stirring at rt under balloon H2 pressure, a NMR spectrum of a worked-up reaction aliquot indicated 80% conversion to the title compound. The reaction was then filtered, the filter cake was washed with 2-propanol (3×10 mL), and the combined clear colorless filtrates were concentrated briefly under rotary evaporation at 50 C. The residue was taken up in DCM and concentrated again to afford the volatile crude title compound (53 mg, 8 1%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 51269-82-0, 5-Chloronicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Player, Mark R.; Lu, Tianbao; Hu, Huaping; Zhu, Xizhen; Teleha, Christopher; Kreutter, Kevin; US2007/225282; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52378-63-9, (3-Aminopyridin-2-yl)methanol, 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, SDS of cas: 52378-63-9, blongs to pyridine-derivatives compound. SDS of cas: 52378-63-9

i. A solution sodium nitrite (2.38 g) in water (10 ml) was added dropwise to a stirred mixture of 3-amino-2-hydroxymethylpyridine (4.8 g) in aqueous hydrochloric acid (48% 10 ml) and water (5 ml) at 0-5 C. This solution of the diazonium salt was added to a hot solution of cuprous chloride (2.5 g) in conc. hydrochloric acid and following cessation of nitrogen evolution the mixture was heated on the steam bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. Filtration, concentration to low bulk and extraction with chloroform yielded 3-chloro-2-hydroxymethyl-pyridine (3.7 g), m.p. 42-44 (from n-pentane).

The synthetic route of 52378-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4024260; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem