Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 14916-63-3, 6-Nitropyridin-2-amine, 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, 14916-63-3, blongs to pyridine-derivatives compound. Computed Properties of C5H5N3O2

Copper (II) chloride (5.8 g) and t-butylnitrite (6.1 ml) were stirred in THF (150 ml) under argon and heated to 65 C. 2-Amino-6-nitropyridine (Shurko, O. P., Mamaev, V. P., Chem Heterocycl Comp, 26, 1990,1 47-52; 5 g, 36 mmol) was added portionwise. The reaction was stirred at 65 C. for 1 hour then allowed to cool to room temperature. EtOAc (200 ml) was added and the organic layer was washed with 2M HCl, water and dried. Volatile material was removed by evaporation to give a sticky orange solid which was triturated with hexane to give the title compound (3.4 g) as a brown/orange solid. NMR: 7.8 (d, 1H), 8.6 (d, 1H), 9.2 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14916-63-3, its application will become more common.

Reference:
Patent; AstraZeneca AB; US6689909; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7169-95-1, Adding some certain compound to certain chemical reactions, such as: 7169-95-1, name is 6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine,molecular formula is C7H6BrN3, 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 7169-95-1.

To a suspension of 6-bromo-2-methyl-[l,2,4]triazolo[1,5-a]pyridine (0.84 g, 4.00 mmol) in anhydrous l,4-dioxane (20 mL) were added Pd2(dba)3 (0.36 g, 0.40 mmol), BINAP (0.49 g, 0.79 mmol), diphenylmethanimine (1.45 g, 8.02 mmol) and t-BuONa (0.77 g, 8.01 mmol). The mixture was degassed and refilled with N2 for several times and heated to 105 C and stirred overnight. The mixture was concentrated in vacuo and the residue was purified by silica chromatography (EtOAc/PE (v/v) = 1/2 to 1/1 to EtOAc 100%) to afford the title compound as brown liquid (0.34 g, yield 27%).MS (ESI, pos. ion) m/z: 313.0 [M+H]+;1H NMR (400 MHz, CDCl3) d (ppm): 7.97-7.92 (m, 1H), 7.76 (d, J = 7.5 Hz, 2H), 7.51 (t, J = 7.3 Hz, 1H), 7.47-7.37 (m, 3H), 7.36-7.28 (m, 3H), 7.14 (dd, J= 7.4, 1.7 Hz, 2H), 6.99 (dd, J = 9.3, 1.8 Hz, 1H), 2.53 (s, 3H).

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. 7169-95-1, 6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2369-19-9, 2-Fluoro-5-methylpyridine, 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, Quality Control of 2-Fluoro-5-methylpyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Fluoro-5-methylpyridine

Diisopropylamine (92 mL) was added to THF (1.2 L), and the mixture was cooled to -18 C. under a nitrogen atmosphere. To this solution was added dropwise a solution (224 mL) of 2.69 M n-butyllithium in hexane. After the dropwise addition, the temperature was increased to -5 C. over 20 minutes while stirring this mixture. The reaction solution was cooled to -73 C. To this reaction solution was added dropwise a THF solution (240 mL) of 2-fluoro-5-methylpyridine (61 g). The reaction mixture was stirred at -75 C. for three and a half hours. To this reaction solution was added dropwise a THF solution (24 mL) of iodine (139 g). The reaction mixture was stirred at -75 C. for 1 hour and 55 minutes. After the reaction, water (220 mL) was added to the reaction solution at the same temperature. The mixture was stirred at the same temperature for 5 minutes. The reaction solution was brought back to room temperature, and then water (1.2 L) was added. To this mixture were added an aqueous solution (300 mL) of sodium thiosulfate pentahydrate (136 g) and water (300 mL), and the mixture was stirred for 10 minutes. This mixture was extracted with MTBE (1.2 L). The organic layer was washed with saturated saline (500 mL). The combined aqueous layers were extracted with MTBE (1 L). The combined organic layers were dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. n-Heptane was added to the residue, and the mixture was cooled. The precipitated solid was collected by filtration. The solid was washed with n-heptane. The filtrate was cooled, and the precipitated solid was collected by filtration. The procedure was repeated 5 times to give the title compound (109.69 g). (0167) 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.29-2.31 (m, 3H), 7.93-8.14 (m, 2H). (0168) ESI-MS m/z 238 [M+H]+

The synthetic route of 2369-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Ozaki, Shunsuke; (31 pag.)US2016/46623; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 166266-19-9 ,Some common heterocyclic compound, 166266-19-9, molecular formula is C6H7IN2, 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.

In a 50 mL resealable tube, a solution of 4-bromothiophenol (3.2 g, 17 mmol, Sigma- Aldrich, India) and 5-iodo-3-methyl-2-pyridinamine (2 g , 8.5 mmol) in DMSO (20 mL) was degassed by purging with argon gas at room temperature for 10 min. Potassium carbonate (3.53 g, 25.6 mmol) and cooper iodide (0.2 g ,1.1 mmol) were added sequentially to the above reaction mixture at room temperature under argon atmosphere The reaction tube was sealed under argon atmosphere and reaction mixture was heated at 150 C for 18 h. The reaction mixture was cooled to room temperature and filtered through a Celite (diatomaceous earth) pad. The filtrate was diluted with cold water (200 mL) and ethyl acetate (100 mL). The EtOAc layer was separated, washed with water, brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue obtained was purified by silica gel (60 to 120 mesh) column chromatography (eluent, 20% EtOAc-hexanes) to give 5-((4- bromophenyl)sulfanyl)-3-methyl-2-pyridinamine (2.7 g) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,166266-19-9, its application will become more common.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 122306-01-8, (6-Bromopyridin-3-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, Quality Control of (6-Bromopyridin-3-yl)methanol, blongs to pyridine-derivatives compound. Quality Control of (6-Bromopyridin-3-yl)methanol

After dissolving the (6-bromo-3-pyridyl)methanol (45.5 g, 0.242 mol) in dimethylformamide (500 ml),tert-butyl diphenylsilyl chloride (69 ml, 0.266 mol) and imidazole (18 g, 0.264 mol) were added while stirring at room temperature. The mixture was stirred at room temperature for an additional 17 hours, 500 ml of water was added and extraction was performed with diethyl ether (500 ml x 2), and then after washing the combined organic layers with brine (500 ml) and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (light yellow syrup, 76.9 g, 74.3%).1H-NMR(CDCl3)delta(ppm) 1.08(9H,s), 4.71(2H,s), 7.34-7.47(6H,m), 7.52(1H,d,J=8.0Hz), 7.65(4H,d,J=8.0Hz), 7.71(1H,d,J=8.0Hz), 8.29(1H,s).

The synthetic route of 122306-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1391451; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 138647-49-1, 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 138647-49-1 as follows.

4-(2,6-dichloropyridin-4-yl)-5,6-dihydropyridine-1(2H)-carbamate 874 mg of 2,6-dichloro-4-(4,4,5,5,-tetramethyl-1,3,2-dioxaboran-2-yl)pyridine, 1.06 g of t-butyl 4-(trifluoromethylsulfonyl oxy)-5,6-dihydropyridine-1(2H)-carbamate, 1.33 g of potassium carbonate and 26 mg of 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex were added in turn to 16 ml of degassed dimethylformamide, and the mixture was stirred at 80 C. for 1.5 hours under argon atmosphere. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 631 mg of the objective compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,138647-49-1, its application will become more common.

Reference:
Patent; NIPPON SHINYAKU CO., LTD.; US2011/288065; (2011); 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.18368-71-3, name is 4-Methyl-2-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.COA of Formula: C6H6N2O2

Method 31; 3-Nitroisonicotinaldehyde 4-Methyl-nitropyridine (1.43g, 10.36mmol) was dissolved in dry DMF (5mL) and dimethylformamide dimethyl acetal (2. 0g, 16. 8mmol) was added. The mixture was heated under nitrogen at 140C for 2 hours and then evaporated under reduced pressure to give (E)- N, dimethyl-2-(3-nitropyridin-4-yl)ethyleneamine as a dark red solid. This was added in one portion at ambient temperature to a stirred solution of sodium periodate (6. 61g, 31mmol) in THF/ 1 1:1 (100mL). After stirring for 2hr at ambient temperature the reaction mixture was filtered and the solid washed with ethyl acetate (100mL). The washings were combined with the filtrate and organic layer separated. The aqueous was extracted with ethyl acetate (2 x lOOmL) and the combined organic layers were washed with saturated aqueous sodium bicarbonate (lOOmL) and brine (lOOmL), dried (MgS04) and evaporated under reduced pressure to give a brown solid which was purified by column chromatography (DCM) to give the title compound. (960mg, 61%). 1HNMR 7. 8 (d, 1H) ; 9. 15 (d, 1H) ; 9. 4 (s, 1H) ; 10. 4 (s, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-71-3, 4-Methyl-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2003/74532; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 79456-33-0, 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. 79456-33-0, name is 5-Chloro-3-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4ClF3N2, 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 B ethyl 6-chloro-8-(trifluoromethyl)imidazo[l,2-a]pyridine-2-carboxylate[0121] 5-chloro-3-(trifluoromethyl)-2-pyridinamine (3.0 g, 15 mmol) and ethyl bromopyruvate (4.27 mL, 30.5 mmol) in N,N-dimethylformamide (50 mL) were stirred at 60 0C for 3 hours. The mixture was allowed to cool and then poured into stirring iced water. The precipitate was stirred for 5 minutes, collected by filtration, washed with water, and dried under vacuum to give the title compound (3.5 g; 78%). LCMS: m/z 293, 295 (M+l).

According to the analysis of related databases, 79456-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna; BASKARAN, Subramanian; CATALANO, John; CHONG, Pek; DICKSON, Hamilton; FANG, Jing; MAUNG, Jack; NEITZEL, Martin, Leon; PEAT, Andy; PRICE, Daniel; RAI, Roopa; ROBERTS, Christopher, Don; SHOTWELL, Brad; TAI, Vincent; ZHANG, Huichang; WO2010/91411; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 82523-07-7, 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.82523-07-7, name is Methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate, molecular formula is C8H7N3O2, molecular weight is 177.16, as common compound, the synthetic route is as follows.

Methyl 3H-imidazo[4,5-c]pyridin-6-carboxylate (44 mg, 0.25 mmol) was dissolved in N,N-dimethylformamide (2 mL) to which potassium carbonate (69 mg, 0.50 mmol) was added and then stirred at room temperature for 10 minutes. Then, benzyl (2R,3S)-2-(3-bromo-2-oxopropyl)-3-(tert-butyldimethylsilyloxy)piperidin-1-carboxylate (120 mg, 0.25 mmol) was added thereto and stirred at room temperature for 3 hours. When the reaction is completed, the solvent was removed, and the resulting mixture was diluted with ethyl acetate and then washed with saturated sodium chloride solution. The organic layer was collected, dried over magnesium sulfate, filtered and concentrated under reduced pressure, and then purified by column chromatography (dichloromethane:methanol=10:1), thereby obtaining the title compound (110 mg, yield: 79%).

The chemical industry reduces the impact on the environment during synthesis 82523-07-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daewoong Pharmaceutical., Ltd.; Park, Joon Seok; Yoon, Youn Jung; Cho, Min Jae; Lee, Ho Bin; Yoo, Ja Kyung; Bong, Yong Lee; (47 pag.)US2017/88551; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 202217-19-4, 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.202217-19-4, name is 6-Chloro-5-methyl-3-nitropyridin-2-amine, molecular formula is C6H6ClN3O2, molecular weight is 187.58, as common compound, the synthetic route is as follows.

(2f) 5-Methyl-3-nitro-6-(2,2,2-trifluoroethoxy)-2- pyridinamine [Formula 23]; 2,2,2-Trifluoroethanol (340 mg, 3.4 mmol) was dissolved in the tetrahydrofuran (10 ml), sodium hydride (60%) (120 mg, 3.0 mmol) was added thereto, and the reaction mixture was stirred for 30 minutes at room temperature under nitrogen atmosphere. A solution of 6-chloro-5-methyl-3-nitro-2-pyridineamine crude product (400 mg) in tetrahydrofuran (10 ml) was dropped, and the reaction mixture was stirred at room temperature for 2.5 days. Water was added to the’ reaction solution and extracted with ethyl acetate, and after washed with a sodium bicarbonate solution, dried over magnesium sulfate. The residue obtained by evaporating the solvent was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n- hexane= 15/85) to yield the title compound (225 mg, 0.90 mmol) as a yellow solid. (at)H NMR (400MHz, DMSO-d6) No. ppm; 2.07 (3H, s), 5.06 (2H, J=9Hz), 8.05 (2H, s), 8.24(1H, s).

The chemical industry reduces the impact on the environment during synthesis 202217-19-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem