Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 153034-86-7, 2-Chloro-4-iodopyridine, 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, 153034-86-7, blongs to pyridine-derivatives compound. name: 2-Chloro-4-iodopyridine

General procedure: An oven dried Schlenk tube was purged with nitrogen and charged with 3-iodopyridine (0.875 mmol, 179.3 mg), BiPh3 (0.25 mmol, 110 mg), K3PO4 (1.5 mmol, 318 mg), Pd(OAc)2 (0.025 mmol, 5.6 mg), PPh3 (0.1 mmol, 26.2 mg) followed by dry DMF (3 mL) under nitrogen atmosphere. The reaction mixture was stirred in an oil bath at 90C for 1h. It was brought to rt, treated with water (10mL), and extracted with ethyl acetate (2×20 mL). The organic extract was treated with brine, dried over anhydrous MgSO4, and concentrated using rotary evaporator under the reduced pressure. The crude was subjected to silica gel column chromatography (5% EtOAc/Hexane) to obtain 3-phenylpyridine (1.1) as colorless oil (115 mg, 98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-86-7, its application will become more common.

Reference:
Article; Rao, Maddali L.N.; Dhanorkar, Ritesh J.; Tetrahedron; vol. 71; 2; (2015); p. 338 – 349;,
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. 7169-97-3, name is N-(5-Bromopyridin-2-yl)acetamide, the common compound, a new synthetic route is introduced below. SDS of cas: 7169-97-3

EXAMPLE 295 5-[3-(3,4,8,9-Tetrahydro-6-methoxy-3,3,8,8-tetramethylfuro[2,3-h]isoquinolin-1-yl)phenyl]-2-pyridinamine A solution of sodium carbonate (198 mg, 1.86 mmol) in water (1 mL) and tetrakis(triphenylphosphine)palladium(0) (55 mg, 0.0475 mmol) were added to a solution of N-(5-bromo-2-pyridinyl)acetamide (243 mg, 1.13 mmol) and 3-cyanophenylboronic acid (249 mg, 1.70 mmol) in 1,2-dimethoxyethane (2 mL) and ethanol (1 mL) and the mixture was stirred at 80 C for 15 hours. Water was poured into the reaction mixture, which was extracted twice with tetrahydrofuran. The combined organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resultant crystals were washed with diethyl ether to obtain N-[5-(3-cyanophenyl)-2-pyridinyl]acetamide (205 mg, yield: 77%). 1H NMR (CDCl3) delta 2.25 (3H, s), 7.54-7.92 (5H, m), 8.02 (1H, br s), 8.32 (1H, d, J = 8.0 Hz), 8.48 (1H, d, J = 2.2 Hz).

The synthetic route of 7169-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1270577; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1659-31-0, 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.1659-31-0, name is Dipyridin-2-yl carbonate, molecular formula is C11H8N2O3, molecular weight is 216.19, as common compound, the synthetic route is as follows.

Step 2 To a suspension of sodium hydride, 60% in mineral oil (0.652 g, 16.31 mmol) in THF (25 mL) was added 3,3-difluoro-2-methylbutan-2-ol (1.84 g, 14.82 mmol) at 0 C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl) carbonate (3.20 g, 14.82 mmol) in THF (25 mL) through a cannula. The formed slurry was stirred at 0 C. for 30 min. The slurry was warmed to rt and stirred for 2 h. The reaction was diluted with EtOAc, washed with brine, dried over MgSO4, filtered, concentrated to give a residue that was purified by Biotage eluting with 10-50% EtOAc in hexanes to afford the desired product 3,3-difluoro-2-methylbutan-2-yl pyridin-2-yl carbonate (500 mg, 13.76%) as an oil that later crystallized to a white solid upon standing. 1H NMR (500 MHz, CHLOROFORM-d) delta 8.43 (ddd, J=4.9, 2.0, 0.7 Hz, 1H), 7.95-7.75 (m, 1H), 7.31-7.24 (m, 1H), 7.15 (dt, J=8.2, 0.8 Hz, 1H), 1.72 (s, 6H), 1.77-1.66 (m, 3H).

The chemical industry reduces the impact on the environment during synthesis 1659-31-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 153034-78-7 ,Some common heterocyclic compound, 153034-78-7, molecular formula is C6H5FIN, 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 solution of diisopropylamine (4.3 mL, 30.5 mmol) in THF (50 mL) at -78 C. was treated with 2.5M n-butyllithium in hexanes (12.2 mL, 30.5 mmol), stirred for 30 minutes, treated dropwise with a solution of 2-fluoro-3-iodo-5-methylpyridine (7.24 g, 30.5 mmol) in THF (30 mL), stirred for 4 hours, quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated to provide 6.3 g (87%) of the desired product. MS (DCI/NH3) m/z 238 (M+H)+; 1H NMR (CDCl3) delta 7.99 (s, 1H), 7.43 (d, 1H), 2.38 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-78-7, its application will become more common.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); 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.942947-95-7, name is 2-Amino-5-bromo-4-chloro-3-nitropyridine, molecular formula is C5H3BrClN3O2, molecular weight is 252.45, as common compound, the synthetic route is as follows.HPLC of Formula: C5H3BrClN3O2

To a solution of tert-butyl 4-(2-(methyl(thiazol-2-yl)amino)-2-oxoethyl)piperazine-1-carboxylate (0.20 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid (2.0 ml). The reaction mixture was stirred at room temperature for 1.5 h, then the solvents were removed under reduced pressure to afford N-methyl-2-(piperazin-1-yl)-N-(thiazol-2-yl)acetamide as the TFA salt that was dried in vacuo. To a mixture of this material (supposedly 0.20 mmol) and isopropanol (3.8 ml) was added 2-amino-5-bromo-4-chloro-3-nitropyridine (0.050 g, 0.20 mmol) followed by diisopropylethylamine (0.126 g, 0.97 mmol). The reaction mixture was stirred at 45 C. for 20 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 20% to 40% ethyl acetate in dichloromethane. The title compound was obtained as a yellow solid (0.042 g, 46%); 1H-NMR (500 MHz, DMSO-d6) 2.69 (br s, 4H, piperazine N(CH2)2), 3.08 (br s, 4H, piperazine N(CH2)2), 3.63 (s, 2H, NCH2CO), 3.70 (s, 3H, N-CH3), 6.98 (s, 2H, NH2), 7.27 (d, J=3.6 Hz, 1H, thiazole H), 7.53 (d, J=3.6 Hz, 1H, thiazole H), 8.17 (s, 1H, 6-H);LC (Method B)-MS (ESI, m/z) Rt=2.75 min-456, 458 [(M+H)+, Br isotopic pattern].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,942947-95-7, 2-Amino-5-bromo-4-chloro-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 115309-57-4, 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.115309-57-4, name is tert-Butyl 6-chloronicotinate, molecular formula is C10H12ClNO2, molecular weight is 213.6608, as common compound, the synthetic route is as follows.

General procedure: To 6-chloronicotinic acid 19a (10 g) in methylene chloride(100 ml) solution, N,N?-diisopropyl-O-tert-butylisourea (50 g) wasadded and the mixture was stirred under heating and reflux for16 h. The insoluble compound was filtered out, and the filtratewas concentrated. The residue was purified by silica gel column chromatography (chloroform/ethyl acetate = 6/1) to obtain the compound 20a (11.66 g). To the compound 20a (6.0 g) in dimethylacetoamide (30 ml) solution, tris(dibenzylideneacetone)dipalladium (0.51 g), zinc cyanide (0.22 g), diphenylphosphinoferrocene (0.62 g), and zinc powder (1.98 g) were added and the mixture was stirred under argon atmosphere at 120 C for 3 h. The reaction solution was filtered by sellite, which was then washed with ethyl acetate. Then, the filtrate was washed with distilled water and saturated saline, then the organic layer was dried over with anhydrous sodium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate= 5/1) to obtain the compound 21a (3.59 g). To copper(I) iodide(0.93 g) in tetrahydrofuran (50 ml) suspension, ethylmagnesium bromide (0.86 M tetrahydrofuran solution)(12.5 ml) was added dropwise under cooling at 0 C, the mixture was stirred at 0 C for 30 min, then the compound 21a (1.0 g) obtained above in tetrahydrofuran (10 ml) solution was added atthe 20 C. After stirring for 30 min at that temperature, 28% ammonia solution in water and ethyl acetate were added to the mixture and the solution separated. The aqueous layer was extracted with ethyl acetate, while the combined organic layer was washed with saturated saline, then was dried over with anhydrous sodium sulfate and concentrated. The obtained residue was purifiedby silica gel column chromatography (hexane/ethyl acetate= 8/1) to obtained the compound 22a (0.47 g). To the compound 22a (200 mg) in tetrahydrofuran (1 ml) solution, (-)-B-chlorodiisopinocampheylborane (65% hexane solution) (0.92 ml) was added dropwise under cooling at 20 C, then the mixture was stirred at that temperature for 18 h. Then, ether and distilled water were added to the reaction mixture, and the solution was separated. The organic layer was extracted with distilled water and 1 M hydrogen chloride. Then, the combined aqueous layer was neutralized by sodium hydrogen carbonate, and extracted with ethyl acetate. Organic layer was washed with saturated saline, then was dried over with anhydrous sodium sulfate and concentrated to obtained the title compound (150 mg, 84% ee). The optical purity was determined using CHIRALCEL AD-H(Daicel Chemical Industries) (movement phase: hexane/ethanol= 98/2, 1.0 ml/min).

Statistics shows that 115309-57-4 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 6-chloronicotinate.

Reference:
Article; Tanaka, Taisaku; Sugawara, Hajime; Maruoka, Hiroshi; Imajo, Seiichi; Muto, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 21; 14; (2013); p. 4233 – 4249;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1289197-78-9, 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 1289197-78-9, name is 2-Bromo-4-chloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Example 195f 4-Chloro-2-(1-oxo-6,7,8,9-tetrahydropyrazino[1,2-a]indol-2(1H)-yl)nicotinaldehyde 195f A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (15 mL), 2-bromo-4-chloronicotinaldehyde 103a (503 mg, 2.28 mmol), 195e (142 mg, 0.76 mmol), cesium carbonate (490 mg, 1.5 mmol), CuI (143 mg, 0.76 mmol), and 4,7-dimethoxy-1,10-phenanthroline (127 mg, 0.52 mmol). After three cycles of vacuum/argon flush, the mixture was heated at 80C for 10 hrs. It was then cooled to room temperature and filtered. The filtrate was washed with brine and concentrated under reduced pressure. The resulting residue was purified with silica-gel column chromatography eluting with 1:4 ethyl acetate/petroleum ether to afford 195f (160 mg, 65%) as a yellow solid. MS-ESI: [M+H]+ 328.

According to the analysis of related databases, 1289197-78-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 111669-25-1, 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. 111669-25-1, name is 1-Boc-4-(3-Aminopyridin-2-yl)piperazine, molecular formula is C14H22N4O2, 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.

Example 34.1 : 4-(3-Ethylamino-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester. To a mixture of 4-(3-amrno-pyridm-2-yl)-piperazme-l-carboxylic acid tert-butyl ester (2,0 g, 7.18 mmol), acetaldehyde (0.81 mL, 0.014 mol) and methanol (30 mL) was added sodium cyanoborohydride (1.36 g, 0.022 mol). The reaction mixture was stirred at room temperature for 2 days and then diluted with ethyl acetate, washed with water and washed with brine. The organic layer was separated, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel using hexanes: ethyl acetate (80:20) to give 4-(3-ethylamino-pyridm-2-yl)-piperazme-l-carboxylic acid tert-butyl ester (2.0 g, 91 %). GC/MS mfz 306, 223, 162, 150, 137, 120, 57.

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 111669-25-1, 1-Boc-4-(3-Aminopyridin-2-yl)piperazine.

Reference:
Patent; ASTRAZENECA AB; WO2008/112440; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 175422-04-5, 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. 175422-04-5, name is 2,6-Dibromo-4-nitropyridine, molecular formula is C5H2Br2N2O2, 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.

P. 2, 6-Dibromo-pyridin-4-ylamine A solution of 15.3 G (54.3 MMOL) 2,6-dibromo-4-nitro-pyridine and 18.5 ml (271.5 MMOL) 25% aq. ammonia in 40 mi tetrahydrofurane was transferred to an autoclave and heated at 95 C for 2.5 h. After cooling to room temperature, the reaction was poured into water (200 mi) and extracted with dichloromethane (3 x 200 ML). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was crystallized from ethyl acetate/petroleum ether to afford 9.6 G (70%) of the title compound as a yellow solid. m. p. 184-186 C.

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 175422-04-5, 2,6-Dibromo-4-nitropyridine.

Reference:
Patent; ALTANA PHARMA AG; WO2005/26164; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 588729-99-1, 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 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Thionyl chloride (60.1 mL, 823 mmol) was added dropwise over 60 min to water (361 mL), cooled to 0 C, maintaining the temperature of the mixture 0-7 C. The solution was allowed to warm to 18 C over 17 h. copper(l) chloride (218 mg, 2.2 mmol) was added to the mixture, and the resultant yellow-green solution was cooled to -3 C using an acetone/ ice bath. 2) HCI (195 mL, 6.418 mol)(37% w/w) was added, with agitation, to 5-bromo-2-chloro-3- pyridineamine (25 g, 121 mmol), maintaining the temperature of the mixture below 30 C with ice cooling. The reaction mixture was cooled to -5 C using an ice/acetone bath and a solution of sodium nitrite (14.72 g, 213 mmol) in water (58 mL) was added dropwise over 45 min, maintaining the temperature of the reaction mixture between -5 to 0 C, the resultant slurry was cooled to -2 C and stirred for 10 min.3) The slurry from step (2) was cooled to -5 C and added to the solution obtained from step 1 ) over 30 min, maintaining the temperature of the reaction mixture between -3 to 0 C ( the slurry from step b was maintained at -5 C throughout the addition). As the reaction proceeded, a solid began to precipitate. When the addition was complete, the reaction mixture was agitated at 0 C for 75 min. The suspended solid was collected by vacuum filtration, washed with water, and dried under vacuum to give 5- bromo-2-chloro- 3-pyridinesulfonyl chloride. ES-LCMS: m/z 271 .94, 269.97 (M-1 ).

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 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna, Lindsey; BOTYANSZKI, Janos; DICKERSON, Scott, Howard; DUAN, Maosheng; LEIVERS, Martin, Robert; MCFADYEN, Robert, Blount; MOORE, Christopher, Brooks; REDMAN, Aniko, Maria; SHOTWELL, John, Bradford; TAI, Vincent, W.-F.; TALLANT, Matthew, David; XUE, Jianjun; WO2012/37108; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem