Tag: M.W:200-300

Reference of 89282-03-1, 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.89282-03-1, name is 3-Iodopyridin-4-ol, molecular formula is C5H4INO, molecular weight is 221, as common compound, the synthetic route is as follows.

General procedure: In a pressure tube, a suspension of 5% Pd/C (5 mol%), 2-bromo-3-hydroxypyridine (0.5 mmol), LiCl (0.5 mmol),cesium carbonate (1 mmol), and terminal alkyne (1.0 mmol)in DMF (3 mL) was stirred for designated period at 150 C.The reaction mixture was filtered, and neutralized with saturatedNH4Cl solution, followed by extraction with ethyl acetate.The crude product was purified by columnchromatography with the use of hexane and ethyl acetate aseluents.The following compounds were prepared with abovedescribed general procedure.

Statistics shows that 89282-03-1 is playing an increasingly important role. we look forward to future research findings about 3-Iodopyridin-4-ol.

Reference:
Article; Park, Hee Jung; Kim, Ji-Eun; Yum, Eul Kgun; Kim, Young Hoon; Han, And Chang-Woo; Bulletin of the Korean Chemical Society; vol. 36; 1; (2015); p. 211 – 218;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 880870-13-3, 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, molecular formula is C6H5BrClNO, 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 solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) andPd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 C for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.? NMR (500 MHz, DMSO-<¾), delta 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC/MS (M+l)+ = 169. According to the analysis of related databases, 880870-13-3, the application of this compound in the production field has become more and more popular. Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; PASTERNAK, Alexander; DEJESUS, Reynalda, K.; TANG, Haifeng; PIO, Barbara; SHAHRIPOUR, Aurash; BELYK, Kevin, M.; CHOBANIAN, Harry, R.; GUO, Yan; FRIE, Jessica, L.; SHI, Zhi-Cai; CHEN, Helen; BLIZZARD, Timothy, A.; CATO, Brian; WO2013/66714; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 351227-42-4, Adding some certain compound to certain chemical reactions, such as: 351227-42-4, name is 6-Chloro-4-iodopyridin-3-amine,molecular formula is C5H4ClIN2, 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 351227-42-4.

Route B : A mixture of 6-chloro-4-iodopyridin-3-ylamine (Preparation 8, 0.33g, 1.30mmol), pyruvic acid (0.27mL, 3.89mmol), DABCO (0.44g, 3.89mmol) and palladium acetate (0.015g, 0.07mmol) in dry DMF was stirred vigorously and degassed with argon for 15min. The reaction mixture was heated to 1070C for 5h. The reaction mixture was allowed to cool to rt and stirred for 16h. The volatiles were removed under reduced pressure and the residue partitioned between EtOAc (10OmL) and water (5OmL). The layers were separated and the aqueous extracted with EtOAc (2x50mL). The combined organics were extracted with aqueous NaOH (2M, 3x70mL). The combined aqueous extracts were acidified to pH 4 by careful addition of glacial acetic acid, then extracted with EtOAc (3x60mL). The combined organics were washed with brine (5OmL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a brown solid. RT=2.72min, m/z (ES+) =197 [M+ H]+

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. 351227-42-4, 6-Chloro-4-iodopyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1000341-55-8, 6-Chloro-3-iodo-1H-pyrrolo[3,2-c]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, SDS of cas: 1000341-55-8, blongs to pyridine-derivatives compound. SDS of cas: 1000341-55-8

Into a 100 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was added a solution of 6-chloro-3-iodo-lH-pyrrolo[3,2-c]pyridine (1.70 g, 6.10 mmol) in N,N-dimethylformamide (20.0 mL) followed by sodium hydride (600 mg, 25.0 mmol). This was followed by addition of 2-iodopropane (2.20 g, 12.9 mmol) dropwise with stirring at 0 C. The reaction mixture was stirred for 16 h at room temperature. The reaction was then quenched by addition of water (50mL). The resulting solution was extracted with ethyl acetate (3×50 mL) and the organic layers were separated and combined. The combined organic layer was washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1 :7) to afford the title compound (1.40 g, 72.0 %) as a yellow solid. LCMS (ESI): RT (min) = 1.549, [M+H]+ = 321, method = M.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1000341-55-8, 6-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 790692-90-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 790692-90-9, name is 6-Chloro-5-iodo-3-nitropyridin-2-amine. A new synthetic method of this compound is introduced below.

The compound 268-100 was prepared as follows. To a solution of 6-chloro-3-nitropyridin-2-amine (630 mg, 3.63 mmol) in ethanol (11 mL) was add I2 (920 mg, 3.62 mmol) and Ag2SO4 (1132 mg, 3.63 mmol).). The resulting solution was stirred overnight at room temperature and dissolved in water (100 mL), then extracted with ethyl acetate (3×80 ml). The combined organic layers were washed with brine (50 ml), dried over anhydrous sodium sulfate and concentrated under vacuum to produce 6-chloro-5-iodo-3-nitropyridin-2-amine as a yellow solid (640 mg, 59%). Next, to a solution of 6-chloro-5-iodo-3-nitropyridin-2-amine (640 mg, 2.14 mmol) in ethanol (40 ml) and water (10 ml) was added Fe powder (1.93 g, 34.46 mmol) and NH4Cl (887 mg, 16.58 mmol). The resulting solution was heated to reflux for 4 h and then concentrated. The residue was dissolved in water (100 mL) and extracted with ethyl acetate (3×80 ml). The combined organic layers was washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 33% ethyl acetate in petroleum ether to produce 6-chloro-5-iodopyridine-2,3-diamine as a brown solid (560 mg, 97%). The mixture of 6-chloro-5-iodopyridine-2,3-diamine (100 mg, 0.37 mmol), (2,3-dichlorophenyl)boronic acid (147.3 mg, 0.77 mmol), Pd(Ph3P)4 (42.9 mg, 0.04 mmol) and sodium carbonate (118.2 mg, 1.12 mmol) in water (5 mL) and dioxane (15 mL) was heated to reflux overnight. Then the resulting solution was quenched with water (100 mL) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 50% ethyl acetate in petroleum ether to produce 6-chloro-5-(2,3-dichlorophenyl)pyridine-2,3-diamine as a brown solid (80 mg, 75%). Finally, the solution of 6-chloro-5-(2,3-dichlorophenyl)pyridine-2,3-diamine (80 mg, 0.28 mmol) in trifluoroacetic acid (10 mL) and hydrochloric acid (conc., 2 mL) was heated to reflux overnight. Then the resulting mixture was quenched with water (100 mL), adjusted pH to 8 with sodium carbonate and extracted with ethyl acetate (3×80 mL). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated to give a residue, which was purified by a silica gel column with 50% ethyl acetate in petroleum ether to produce 5-chloro-6-(2,3-dichlorophenyl)-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine. Trifluoroacetic acid as a off-white solid (2 mg, 2%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,790692-90-9, its application will become more common.

Reference:
Patent; MERIAL LIMITED; Meng, Charles Q.; US2013/281392; (2013); A1;,
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. 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate, molecular formula is C8H8BrNO2, 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. Computed Properties of C8H8BrNO2

Step 1 To a solution of 5-bromo-4-methylpyridine-2-carboxylic acid methyl ester (2.207 g, 9.59 mmol), 4-methoxylphenylboronic acid (1.604 g, 10.55 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (0.313 g, 0.480 mmol) in THF (30 mL) was added potassium carbonate (2.0 M in water, 10.1 mL, 20.15 mmol). The mixture was purged with nitrogen and heated at 50 C. for 1 hour and at 60 C. for 5 hours. The reaction was poured into ethyl acetate and was washed with brine, dried over sodium sulfate, filtered and concentrated. It was purified by column chromatography to yield methyl 5-(4-methoxyphenyl)-4-methylpyridine-2-carboxylate (2.47 g, 9.59 mmol) as a pink solid. MS ESI calc’d. for C15H16NO3 [M+H]+ 258.1. found 258.1.

With the rapid development of chemical substances, we look forward to future research findings about 886365-06-6.

Reference:
Patent; Shao, Pengcheng Patrick; Sun, Wanying; Katipally, Revathi Reddy; Vachal, Petr; Ye, Feng; Liu, Jian; Sha, Deyou; US2013/109649; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14121-36-9, 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. 14121-36-9, name is 2,3,4,6-Tetrachloropyridine, molecular formula is C5HCl4N, 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 1: 100g of tetrachloropyridine, 0.5g of catalyst, 15g of acid binding agent,3g of auxiliary agent and 500g of organic solvent are placed in a 1L autoclave, and the autoclave is evacuated three times until the autoclave is in a vacuum state;The tetrachloropyridine is 2,3,4,6-tetrachloropyridine;The catalyst includes a supported activated carbon, a metal M1, a metal M2, and a metal M3 supported on the supported activated carbon,The metal M1 is Pd, the metal M2 is Ag, and the metal M3 is V,The mass percentage content of metal M1 in the catalyst is 2%, and the mass percentage content of metal M2 is 0.4%.The mass percentage of metal M3 is 0.15%; The acid binding agent is triethylamine and urea, and the mass ratio of the triethylamine and urea is 1: 1;The auxiliary is citric acid;The organic solvent is ethyl acetate; Step 2: Replace the high-pressure reactor after vacuuming in Step 1 with nitrogen for three times, and then replace with hydrogen for three times;Step three, continue to introduce hydrogen into the autoclave after the hydrogen replacement in step two, control the hydrogen pressure to 1.0 MPa, the temperature to 50 C., and react for 7 hours under the stirring condition, and reduce to room temperature;Step 4: Drain the hydrogen in the autoclave after the temperature drops to room temperature in Step 3, replace it with nitrogen for three times, filter the system in the autoclave to obtain the filtrate and the recovered catalyst, and reuse the recovered catalyst; Step 5. Distillate the filtrate in step 4 under reduced pressure to obtain 2,3-dichloropyridine as a white solid.The solvent obtained by vacuum distillation is recovered and reused; the vacuum of the vacuum distillation is -0.092 MPaThe temperature of the vacuum distillation was 40 C. The yield of 2,3-dichloropyridine was 98.1%, and the purity was 99.3%.

According to the analysis of related databases, 14121-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Kaili New Materials Co., Ltd.; Li Xiaoan; Xiao Dawei; Han Bin; Zhang Yu; Zhang Zhixiang; Zeng Yongkang; Wan Kerou; Gao Wu; (13 pag.)CN110759859; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1111637-94-5, 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. 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, 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 solution of 5-bromo-3-methyl-lH-pyrrolo[2,3-b]pyridine (20 g, 94.8 mmol) in NN-dimethylformamide (200 mL) was added potassium acetate (27.9 g, 284.4 mmol) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (28.8 g, 113.74 mmol). The resulting mixture was degassed with nitrogen for 5 min, l,l’-Bis(diphenylphosphino)ferrocene-palladium(n)dichloride (6.65g, 9.48mmol) was added and the mixture was degassed with nitrogen once more for 5 min. The reaction mixture was stirred overnight at 80-90 C. The reaction mixture was poured into water, extracted with (3 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 9% to 50% ethyl acetate in petroleum ether) affording 3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine as a white solid (10.5 g, 43%): NMR (400MHz, DMSO-d6), delta 11.360 (s, 1H), 8.371-8.375 (d, /= 1.6 Hz, 1H), 8.097-8.100 (s, /= 1.2 Hz, 2H), 7.17 (s, 1H), 3.296 (s, 3 H), 1.245 (s, 12H).

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 1111637-94-5, 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1289131-55-0, 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 1289131-55-0, name is 4-Bromo-2-(2-methoxyethoxy)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-bromo-2-(2-methoxyethoxy)pyridine (for a preparation see Intermediate 37, 306 mg, 1.319 mmol), 5/s(pinacolato)diboron (1004 mg, 3.96 mmol), PdCI2(dppf) (96 mg, 0.132 mmol) and potassium acetate (388 mg, 3.96 mmol) in 1 ,4-dioxane (10 mL) was heated in a microwave at 100C for 30 min. The reaction was diluted with ethyl acetate and filtered through a Celite column. The filtrate was evaporated to give 2-(2-methoxyethoxy)-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)pyridine as a brown residue. The yield was assumed to be 100 % (368 mg, 1.319 mmol). The material was used crude in the next stage without further purification. LCMS (2 min, Formic): Rt = 0.44 min, MH+ 198 (observed mass ion is consistent with hydrolysis to boronic acid under LCMS conditions).

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 1289131-55-0, 4-Bromo-2-(2-methoxyethoxy)pyridine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1235036-15-3, Adding some certain compound to certain chemical reactions, such as: 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate,molecular formula is C10H11BrClNO2, 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 1235036-15-3.

A mixture of Example 5C (0.736 g), Example 5B (1.62 g), and Cs2C03 (4.1 g) in N,N- dimethylformamide (15 mL) was heated at 120 C for 12 hours, cooled, diluted with ethyl acetate, and acidified with 10% citric acid. The organic layer was washed with water and brine, dried over Na2S04, filtered and concentrated. The residue was purified by silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes, to provide the title compound.

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. 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; JUDD, Andrew S.; SOUERS, Andrew J.; TAO, Zhi-Fu; WO2014/28381; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem