Tag: M.W:200-300

Synthetic Route of 65550-78-9 ,Some common heterocyclic compound, 65550-78-9, molecular formula is C6H5BrIN, 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. 5-Iodo-3-methyl-2-methoxy-pyridine. To a solution containing 2-bromo-5-iodo-3-methyl-pyridine (4.80 g, 16.0 mmol) in DMSO (15 ML) is added methanolic NaOMe (3.33 M, 5.3 ML, 17.7 mmol) at 0 C. The solution is allowed to warm to ambient temperature and then heated at 70 C. for 1 hour.The reaction mixture is diluted with diethyl ether (300 ML) and water (200 ML) and the layers are separated.The organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated.The crude product is purified by silica gel flash column chromatography (hexane/diethyl ether, 19:1) to provide 2.86 g (71%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3) delta2.12 (s, 3H), 3.90 (s, 3H), 7.60 (d, J=2.1 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H) ppm; MS (EI): m/z 249 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65550-78-9, its application will become more common.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; US2004/102450; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1206775-52-1, 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. 1206775-52-1, name is 5-Bromo-6-methoxypicolinaldehyde. A new synthetic method of this compound is introduced below.

Preparation 79(5-B romo-6-methoxypyrid i n-2-yl)-N-methyl methanam ine5-Bromo-6-methoxypicolinaldehyde of preparation 78 (69 mg, 0.32 mmol) in a solution of NH2CH3 in THF (2M, 3ml_) was stirred under nitrogen at room temperature for 45 mins, and LCMS showed a mass of 230 which indicated the presence of the iminium ion. Sodium borohydride (36.2 mg, 0.957 mmol) was added, and the reaction was stirred at room temperature overnight. The desired product was detected by LCMS, and the reaction was quenched with MeOH (0.5 mL) and water (10ml), then partitioned with EtOAc (10 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to give the title compound as a yellow oil (47 mg), which was taken into the next step without further purification.MS: ESI+ m/z 231 [MH]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1206775-52-1, 5-Bromo-6-methoxypicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, Computed Properties of C6H8BrN3, blongs to pyridine-derivatives compound. Computed Properties of C6H8BrN3

[00135] 5-Bromo-N*2*-methyl-pyridine-2,3-diamine (0.85 g, 4.55 mmol) is dissolved in trimethylorthoformate (12 mL) and the solution is heated to reflux for 3h, then cooled and evaporated to dryness. The solid residue is purified by flash column chromatography to give the title compound as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; WEIL, Tanja; HECHENBERGER, Mirko; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; ERDMANE, Elina; SMITS, Gints; WO2011/15343; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 669066-89-1, 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. 669066-89-1, name is 3-Amino-5-bromopicolinamide, molecular formula is C6H6BrN3O, 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 2: 3-Amino-5-bromo-pyridine-2-carboxylic acid To a 100 mL round bottom flask, 3-amino-5-bromo-pyridine-2-carboxylic acid amide (1.05 g, 0.0049 mol) and aqueous sodium hydroxide solution (0.98 g in 10 mL water, 0.0245 mol) was added. The reaction mixture was stirred at reflux temperature for 5 h. The volatiles were evaporated under reduced pressure to get the residue. The residue was neutralized to pH = 7.0, using 2N HC1 at 0C to obtain the precipitate. The precipitate was filtered and dried to get the title compound as light yellow solid [1 g, 95%]. 1H NMR (300 MHz, DMSO-d6): delta 7.65 (d, J = 2.1 Hz, 1H), 7.20 (d, J = 2.1 Hz, 1H), 7.01-7.16 (brs, 2H); LC-MS (ESI): Calculated mass: 215.9; Observed mass: 217.0 [M+H]+ (RT: 0.43 min).

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 669066-89-1, 3-Amino-5-bromopicolinamide.

Reference:
Patent; ENDO PHARMACEUTICALS INC.; SMITH, Roger, Astbury; THOMPSON, Scott, Kevin; HOSAHALLI, Subramanya; BEJUGAM, Mallesham; NANDURI, Srinivas; PANIGRAHI, Sunil, Kumar; MAHALINGAM, Natarajan; WO2012/58671; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 29241-65-4, 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 29241-65-4, name is 5-Bromo-2-chloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromo-2-chloronicotinic acid (50 g, 211 mmol) in MeOH (200 mL) was added H2SO4 (20.7 g, 211.46 mmol) at 25 C. The mixture heated to 90 C and stirred for 12 hours. LCMS showed that the reaction was complete. The reaction was neutralized with Na2CO3 to pH = 7-8 and concentrated under reduced pressure to remove MeOH. The residue was extracted with EtOAc (300 mL x 3). The combined organic layer was concentrated under reduced pressure to give methyl 5-bromo-2-chloronicotinate (45 g, 180 mmol, 85% yield) as a brown solid. ESI-MS (m/z): 249.9 (M+H)+

According to the analysis of related databases, 29241-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17570-98-8 ,Some common heterocyclic compound, 17570-98-8, molecular formula is C7H7Br2NO, 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.

General procedure: Compounds 17-29and 43-61 were prepared following this general protocol unless otherwise noted. To substituted2-bromoethanone in ethanol was added substituted thiourea (1.02 eq). The mixture wasstirred at 70C. The reaction was monitored via LC/MS. After 2 h, the reaction mixture wascooled to room temperature and precipitate was formed. The precipitate was collected by vacuumfiltration and washed with acetone. The solid was dissolved in 2 MNaOH (25 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layers were dried over Na2SO4 andconcentrated in vacuo desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17570-98-8, its application will become more common.

Reference:
Article; Kesicki, Edward A.; Bailey, Mai A.; Ovechkina, Yulia; Early, Julie V.; Alling, Torey; Bowman, Julie; Zuniga, Edison S.; Dalai, Suryakanta; Kumar, Naresh; Masquelin, Thierry; Hipskind, Philip A.; Odingo, Joshua O.; Parish, Tanya; PLoS ONE; vol. 11; 5; (2016);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 77837-09-3, Adding some certain compound to certain chemical reactions, such as: 77837-09-3, name is Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate,molecular formula is C13H11NO3, 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 77837-09-3.

After 750 mg (3.27 mmol) of methyl 6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylate was dissolved in 9 mL of methanol and 3 mL of water, 235 mg (9.81 mmol) of lithium hydroxide was added to the solution. Afterward, the resulting reaction solution was stirred at about 50C for about 5 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo, followed by addition of aqueous HCl to titrate a pH of the reaction product to pH 2. After filtration of the resulting solid compound (Actual yield: 470 mg, Percent yield: 67 %), the resulting compound was used without purification.[60] 1H-NMR(DMSO-d6,200MHz)delta8.18(s,1H),7.88(d,1H),7.49(m,5H),6.54(d,2H)

According to the analysis of related databases, 77837-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SK BIOPHARMACEUTICALS CO., LTD.; MAENG, Cheol Young; JANG, Young Koo; CHA, Su Bong; SHIN, Hye Won; JOUNG, Chan Mi; CHA, Hwa Ryun; YI, Eun Jung; WO2012/102580; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 100397-96-4 ,Some common heterocyclic compound, 100397-96-4, molecular formula is C13H10BrNO, 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.

2) (E)-1-(4-bromophenyl)-3-(dimethylamino)-2-(pyridin-4-yl)prop-2-en-1-one A mixture of 1-(4-bromophenyl)-2-(pyridin-4-yl)ethanone (500 mg, 1.811 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (1 g, 8.39 mmol) in DMF (9 ml) was heated to 100 C. for about 6 h. Removal of the solvent under reduced pressure provided (E)-1-(4-bromophenyl)-3-(dimethylamino)-2-(pyridin-4-yl)prop-2-en-1-one (640 mg, 1.546 mmol, 85% yield) as a red oil which was used in the next step without further purification. LC-MS (Method B): m/z 331 (M+H), RT: 1.37 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100397-96-4, its application will become more common.

Reference:
Patent; GENESTE, Herve; TURNER, Sean Colm; OCHSE, Michael; DRESCHER, Karla; BLACK, Lawrence A.; JANTOS, Katja; US2014/148461; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 880870-13-3, 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 880870-13-3 as follows.

Step 1: Preparation of l-(4-(6-chloro-4-methoxypyridin-3-yl)-2-fluorophenyl)pyrrolidin-2- one. [0802] A mixture of 5-bromo-2-chloro-4-methoxypyridine (219 mg, 0.983 mmol), l-(2- fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one (300 mg, 0.983 mmol), Pd(dppf)Cl2 (72 mg, 0.098 mmol) and Na2C03 (313 mg, 2.95 mmol) in dioxane (4 mL) and water (1 mL) was degassed and purged with N2 for 3 times. And the resulting reaction mixture was stirred at 90 C for 4 hours under N2 atmosphere. A black suspension was formed. LCMS showed the purity of the desired product is 63% (Rt = 0.823 min; MS Calcd: 320.1; MS Found: 320.9 [M+H]+). The reaction mixture was diluted with water (10 mL). The aqueous layer was extracted with EtOAc (30 mL x3). The combined organic layer was washed with water (20 mL x2), brine (40 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by Combi Flash (20% to 80% EtOAc in PE) to give 1-(4-(6-chloro-4-methoxypyridin-3-yl)-2-fluorophenyl)pyrrolidin-2-one (230 mg, yield: 78%) as a yellow solid. NMR (400 MHz, CDCb) d 2.20-2.28 (2H, m), 2.60 (2H, t, J= 8.0 Hz), 3.84-3.89 (2H, m), 3.90 (3H, s), 6.92 (1H, s), 7.24-7.33 (2H, m), 7.49 (1H, t, J= 8.0 Hz), 8.19 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,880870-13-3, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; KESICKI, Edward A.; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (450 pag.)WO2019/126731; (2019); 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. 77837-09-3, name is Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate. A new synthetic method of this compound is introduced below., HPLC of Formula: C13H11NO3

General procedure: Example 1-3 Synthesis of 6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylic acid [0042] After 750 mg (3.27 mmol) of methyl 6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylate was dissolved in 9 mL of methanol and 3 mL of water, 235 mg (9.81 mmol) of lithium hydroxide was added to the solution. Afterward, the resulting reaction solution was stirred at about 50° C. for about 5 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo, followed by addition of aqueous HCl to titrate a pH of the reaction product to pH 2. After filtration of the resulting solid compound (Actual yield: 470 mg, Percent yield: 67percent), the resulting compound was used without purification. [0043] 1H-NMR (DMSO-d6,200 MHz) delta8.18 (s, 1H), 7.88 (d, 1H), 7.49 (m, 5H), 6.54 (d, 2H)

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, 77837-09-3, Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate.

Reference:
Patent; SK BIOPHARMACEUTICALS CO., LTD.; Maeng, Cheol Young; Jang, Young Koo; Cha, Su Bong; Shin, Hye Won; Joung, Chan Mi; Cha, Hwa Ryun; Yi, Eun Jung; US2013/317059; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem