Tag: M.W:100-200

Application of 1658-42-0, 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 1658-42-0 as follows.

General procedure: An oven-dried Schlenk tube was charged with Pd(OAc)2 (0.015 mmol, 3.4 mg), X-Phos (0.015 mmol, 7.2 mg), Cs2CO3 (0.9 mmol, 293 mg), substrate 1 (0.3 mmol) and 2 (0.4 mmol). The reaction vessel was evacuated and backfilled again with nitrogen gas, and 1,4-dioxane (1 mL) was added via syringe under nitrogen. The reaction mixture was stirred at 100 C for 12 hours. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The crude was nextfiltered through a plug of celite, which was washed with ethyl acetate. The solution was concentrated and further purifiedby flash column chromatography to afford the corresponding product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1658-42-0, its application will become more common.

Reference:
Article; Jin, Chaochao; Xu, Kun; Fan, Xiao; Liu, Changyao; Tan, Jiajing; Chinese Chemical Letters; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 123148-66-3 ,Some common heterocyclic compound, 123148-66-3, molecular formula is C7H9NO2, 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.

C) 2-methoxyisonicotinaldehyde To a solution of (2-methoxypyridin-4-yl)methanol (6.74 g) and triethylamine (67.5 mL) in DMSO (200 mL) was added sulfur trioxide pyridine complex (30.8 g), and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After silica gel filtration, the solvent was evaporated under reduced pressure to give a crude product of the title compound (4.33 g) as a brown oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,123148-66-3, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; EP2816032; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Dimethyl pyridine-2,5-dicarboxylate

To a mixture of dimethyl pyridine-2,5-dicarboxylate (3.08 g, 15.78 mmol) and calcium chloride (7.01 g, 63.1 mmol) in tetrahydrofuran (33 mL) and EtOH (67 mL) was added sodium borohydride (1 .493 g, 39.5 mmol) in portions at 0 C. The reaction mixture was stirred at 0 C for 12 hrs. The mixture was poured into ice/water, was diluted with dichloromethane (400 ml.) and stirred vigorously for 15 minutes. The separated organic layer was dried over magnesium sulfate, filtered off and concentrated under reduced pressure providing methyl 6-(hydroxymethyl)nicotinate (1 .2 g) as an off white solid, which was directly used in the next step without further purification. LCMS (m/z): 168.0 [M+H]+; Rt = 0.26 min

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 881-86-7, Dimethyl pyridine-2,5-dicarboxylate.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; NG, Simon, C.; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WO2012/101064; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75711-00-1 , The common heterocyclic compound, 75711-00-1, name is 2-Chloro-3-methoxy-5-nitropyridine, molecular formula is C6H5ClN2O3, 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.

Synthesis of 3-methoxy-2-(4-methyl-lH-imidazol-l-yl)-5-nitropyridine [0328] To a stirred solution of 2-chloro-3-methoxy-5-nitropyridine (2 g, 10.60 mmol) in DMSO (40 mL) under argon atmosphere were added potassium carbonate (3.65 g, 26.51 mmol) and 4-methyl-lH-imidazole (1 g, 12.72 mmol) at RT. The reaction mixture was stirred at 45 C for 16 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with hot water (40 mL). The obtained solid was filtered and dried in vacuo to afford 3-methoxy-2-(4-methyl-lH-imidazol-l-yl)-5-nitropyridine (1.8 g, 72%) as a yellow solid. 1H-NMR (DMSO-<, 400 MHz): delta 8.92-8.90 (m, 1H), 8.45 (s, 1H), 8.36-8.32 (m, 1H), 7.68 (s, 1H), 4.10 (s, 3H), 2.20 (s, 3H); LC-MS: 235 (M+l); (column; X-Bridge C- 18 (50 3.0 mm, 3.5 mu); RT 2.09 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH:CH2Cl2 (R 0.4). The synthetic route of 75711-00-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15855-06-8, 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. 15855-06-8, name is 2-Chloro-6-methoxypyridine-4-carboxylic Acid. A new synthetic method of this compound is introduced below.

BH3. DMS (1.0 mL, 10.66 mmol) was refluxed in THF (20 mL) for 30 min (formation of BH3. THF). At RT, Example 17 (2.0 g, 10.66 mmol in 10 mL THF) was added dropwise, and then the reaction mixture was heated to reflux for 3 h. The solution was allowed to cool to ambient temperature, solid sodium carbonate (0.5 g) and water (5 mL). The resulting mixture was heated for a short while and poored in water (50 mL). Extraction with ethyl acetate (3 x 50 mL), drying of the combined organic layers (Na2SO4) and evaporation in vacuo gave a 1: 1 mixture of starting material and product. Purification by flash column chromatography over silica gel eluting with ethyl acetate gave 780 mg (42 %) of an off-white solid. IH NMR (400 MHz, CDC13) 8 3.92 (s, 3H) 4.66 (s, 2H) 6.64 (s, 1H) 6.89 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15855-06-8, 2-Chloro-6-methoxypyridine-4-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; BIOVITRUM AB; WO2004/63156; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 19798-80-2, name is 4-Chloropyridin-2-amine. A new synthetic method of this compound is introduced below., Formula: C5H5ClN2

Step 1 : To a solution of 4-chloropyridin-2-amine (3 g, 23.2 mmol) in DMSO (60 mL) was added sodium methoxide (12.6 g, 232 mmol) and the mixture was then stirred at 150 C for 3 hours then poured into ice- water. The product was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2S04) and concentrated. The residue was purified by silica gel chromatography using a solvent system of 50% petroleum ether/EtOAc to give 4-methoxypyridin-2 -amine (460 mg, 16%) as a yellow solid MS ESI calcd for C6H8N20 [M + H]+ 125, found 125.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 19798-80-2, 4-Chloropyridin-2-amine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ROMEO, Eric Thomas; MACHACEK, Michelle, R.; TROTTER, Benjamin Wesley; MILLER, Thomas Allen; ANDRESEN, Brian Michael; ANTHONY, Neville John; TAOKA, Brandon, M.; LIU, Yuan; WO2012/151137; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56129-55-6, Adding some certain compound to certain chemical reactions, such as: 56129-55-6, name is 1-(Pyridin-3-yl)ethanamine,molecular formula is C7H10N2, 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 56129-55-6.

General procedure: To a solution of ethyl 2- chlorothieno[3,2-(/Jpyrimidine-4-carboxylate (100 mg, 0.41 mmol) and DIEA (0.22 mL, 1.23 mmol) in NMP (3 mL) was added (6-methoxypyridin-3-yl)methanamine hydrochloride (commercially obtained from PharmaBlock, Sunnyvale, CA) (97 mg, 0.89 mmol). The reaction mixture was stirred at 130 C for 3 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with 25% aqueous NaCl solution, then with brine three times and dried. The solvent was evaporated and the residue was purified by flash chromatography (24g, HP silica, Teledyne Isco) eluting with 2% to 100% solvent A (DCM/MeOH/NH4OH, 100/10/1) in DCM to provide 2-chloro-N-((6-methoxypyridin-3- yl)methyl)thieno[3,2-Patent; CORVUS PHARMACEUTICALS, INC.; LI, Zhihong; FILONOVA, Lubov, Konstantinovna; BRADLEY, Erin, Kathleen; VERNER, Erik; (816 pag.)WO2019/46784; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-63-3, 2-Chloro-6-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, Application In Synthesis of 2-Chloro-6-methylpyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Chloro-6-methylpyridine

Intermediate 691 ,1 -Dimethylethyl r2-(4-{(2S,4/?)-1 -acetyl-2-methyl-4-r(6-methyl-2-pyridinyl)aminol-1 ,2,3,4- tetrahvdro-6-quinolinyl)-1 /-/-pyrazol-1 -yl)ethyllmethylcarbamateA flask was charged with 2-chloro-6-methylpyridine (141 mg, 1 .103 mmol) and treated at room temperature under nitrogen with 1 ,1 -dimethylethyl [2-(4-{(2S,4/?)-1 -acetyl-2-methyl- 4-amino-1 ,2,3,4-tetrahydro-6-quinolinyl}-1 H-pyrazol-1 -yl)ethyl]methylcarbamate (for a preparation see intermediate 55) (228 mg, 0.551 mmol) in 1 ,4-dioxane (5 mL). 2′- (dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos) (43.4 mg, 0.1 10 mmol), sodium tert-butoxide (106 mg, 1 .103 mmol) and tris(dibenzylideneacetone)dipalladium(0) (50.5 mg, 0.055 mmol) were added and the resulting mixture was stirred at 1 10C for 16 h then cooled to room temperature and partitioned between AcOEt (25 mL) and water (25 ml_). The layers were separated and the organic phase was washed with water (25 mL) then dried over Na2S04 and concentrated in vacuo. Purification of the residue on SP4 using a 50 G silica cartridge (gradient: 1 to 5% MeOH in DCM) gave 1 ,1 -dimethylethyl [2-(4-{(2S,4R)-1 -acetyl-2- methyl-4-[(6-methyl-2-pyridinyl)amino]-1 ,2,3,4-tetrahydro-6-quinolinyl}-1 H-pyrazol-1 – yl)ethyl]methylcarbamate (107.9 mg, 0.198 mmol, 35.8 % yield) as a brown oil.LCMS (Method B): Retention time 0.79 min, [M+H]+ = 519.20

The synthetic route of 18368-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GOSMINI, Romain, Luc, Marie; WO2011/54848; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate, 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, HPLC of Formula: C8H7NO3, blongs to pyridine-derivatives compound. HPLC of Formula: C8H7NO3

Reference Example 28 Methyl 6-(2-tert-butyl-5-chloro-6-methoxy-1H-indol-3-ylmethyl)pyridine-2-carboxylate To a solution of triethylsilane (0.202 mL) and trifluoroacetic acid (0.049 mL) in dichloromethane (2 mL) was added a suspension of 2-tert-butyl-5-chloro-6-methoxy-1H-indole (100 mg) and methyl 6-formylpyridine-2-carboxylate (76.2 mg) in dichloromethane (1.5 mL) under ice-cooling, and this mixture was stirred at room temperature overnight. To the reaction mixture was added water, and then the resulting mixture was alkalified by the addition of sodium hydrogen carbonate. The organic layer was separated and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (152 mg). 1H-NMR (CDCl3) delta ppm: 1.39 (9H, s), 3.90 (3H, s), 4.05 (3H, s), 4.52 (2H, s), 6.91 (1H, s), 6.95-7.05 (1H, m), 7.28 (1H, s), 7.60 (1H, t, J=7.8 Hz), 7.80-8.20 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Tatani, Kazuya; Kondo, Atsushi; Kondo, Tatsuhiro; Kawamura, Naohiro; Seto, Shigeki; Kohno, Yasushi; US2013/317065; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1681-37-4 ,Some common heterocyclic compound, 1681-37-4, molecular formula is C5H5N3O2, 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.

To a solution of 4-amino-3-nitropyridine (2.0 mmol) in DMF (10 mL), NaH (2.2 mmol) was addedslowly, the mixture was stirred at room temperature for 30 min. Then ethyl iodine (2.0 mmol) wasadded slowly into the mixture until the reaction is finished monitored by TLC. Then the solvent wasevaporated and the residue was purified by silica gel chromatography by DCM/MeOH system toafford 4-ethylamino-3-nitropydine.To a solution of 4-ethylamino-3-nitropydine (1.0 mmol) in EtOH (10 mL), 10% Pd/C was added.Then the mixture was reduced by catalytic hydrogenation. Until the completion of the reaction,the Pd/C was filtered and the solvent was evaporated. The product was used in the next step withoutfurther purification.The solution of substituted 4-ethylamino-3-aminopydine (0.5 mmol), benzaldehyde (0.5 mmol)with sodium pyrosulfite (0.5 mmol) was stirred in DMF (8 mL) under 120 C overnight. On completionof the reaction, the solvent was evaporated and the residue was purified by silica gel chromatographyby DCM/MeOH system to afford the final product. If necessary, the crude product could berecrystallized in DCM to afford pure compound [31].

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. 1681-37-4, 4-Amino-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pan, Liangkun; Hang, Nan; Zhang, Chao; Chen, Yu; Li, Shuchun; Sun, Yang; Li, Zhongjun; Meng, Xiangbao; Molecules; vol. 22; 2; (2017);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem