Tag: M.W:100-200

Application of 63071-09-0 ,Some common heterocyclic compound, 63071-09-0, molecular formula is C7H9NO, 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.

Commercially available 2,3-lutidine (5.00 g) was dissolved in dichloromethane (50 ml) and the solution was cooled to 0C. After that, the solution was added with meta-chloroperbenzoic acid (12.1 g) and then stirred at room temperature for 2 hours. After completion of the reaction, the solution was added with dichloromethane and washed with a 1 mol/l sodium hydroxide aqueous solution and saturated saline solution, followed by drying with anhydrous sodium sulfate. Then, the solvent was distilled off, thereby obtaining crude 2,3-lutidin-N-oxide (3.16 g). A 2.00 g part thereof was dissolved in dichloromethane (40 ml) and then the solution was cooled to 0C. Subsequently, the solution was added with trifluoroacetic anhydride (4.49 ml), followed by stirring at room temperature for 4 hours and then at 45C for 3 hours. After completion of the reaction, the solvent was distilled off and the residue was dissolved in methanol (30 ml), followed by the addition of a sodium methoxide/methanol solution until the pH of the solution would reach pH = 10. After the solution had been stirred at room temperature for 1 hour, the solvent was distilled off and extraction was then carried out with dichloromethane. The extract was dried with anhydrous sodium sulfate and the solvent was then distilled off, thereby obtaining 3-methyl-2-hydroxymethylpyridine (1.30 g). A 605.3 mg part thereof was dissolved in chloroform (30 ml) and then added with manganese dioxide (chemically processed product) (3.03 g), followed by stirring at 70C for 2 hours. After completion of the reaction, the catalyst was removed through Celite filtration and the solvent was then concentrated. Then, the residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (419.8 mg) as a pale-orange colored liquid. MS(FAB,Pos.):m/z=122[M+H]+1H-NMR(500MHz,CDCl3):delta=2.67(3H,s),7.40(1H,dd,J=7.8,4.6Hz),7.64(1 H,d,J=7.8Hz),8.67(1H,d,J=4.6Hz),10.2(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,63071-09-0, its application will become more common.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 91940-84-0, 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 91940-84-0, name is 2-(tert-Butyl)isonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 3: Preparation of benzyl (1R,3R,5R)-2-(2-(tert-butyl)isonicotinoyl)-2-azabicyclo[3.1.0]hexane-3-carboxylate Benzyl (1R,3R,5R)-2-azabicyclo[3.1.0]hexane-3-carboxylate hydrochloride (0.450 g, 1.36 mmol), O-(Benzotriazol-1-yl)-N,N,N’N’-tetramethyluronium hexafluorophosphate (0.78 g, 2.04 mmol), benzotriazol-1-ol (0.28 g, 2.04 mmol) and 2-(tert-butyl)isonicotinic acid (0.269 g, 1.50 mmol) were added to a flask and NMP (5.0 mL) was added, followed by N,N-diisopropylethylamine (0.71 mL, 4.08 mmol). The resulting mixture was stirred at 22 C. for 20 minutes. The reaction was diluted with EtOAc (60 mL) and saturated NaHCO3 (70 mL) solution. The layers were shaken vigorously and the organic phase was washed again with saturated NaHCO3 solution, twice with water, and once with saturated sodium chloride solution. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The remaining viscous oil was purified by MPLC using silica gel and eluted with a gradient of 0-30% EtOAc/hexanes, providing benzyl (1R,3R,5R)-2-(2-(tert-butyl)isonicotinoyl)-2-azabicyclo[3.1.0]hexane-3-carboxylate (0.386 g, 1.02 mmol) as a colorless glassy solid. LCMS-APCI (POS.) m/z: 379.2 (M+H)+.

According to the analysis of related databases, 91940-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89182-17-2, 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. 89182-17-2, name is 6-Chloro-3,4-pyridinediamine, molecular formula is C5H6ClN3, 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.

Synthesis of (6-chloro-1H-imidazo[4,5-c]pyridin-2-yl)benzylamine A solution of benzylthioisocyanate (7.0 mL, 53.1 mmol) and 6-chloro-pyridine-3,4-diamine (7.6 g, 53.1 mmol) in CHCl3 (110 mL) was heated at 50 C for 12 h. After cooling to ambient temperature, the reaction mixture was treated with EDC (12.2 g, 63.7 mmol) and Et3N (8.9 mL, 63.7 mmol). The reaction mixture was then stirred at room temperature for additional 18 h. CHCl3 (110 mL) was added to the reaction mixture, followed by water (110 mL) and the organic phase was separated. The aqueous phase was re-extracted with CHCl3 (2 x 150 mL) and the combined organic layers were washed with brine (50 mL). The organic layers were dried over Na2SO4, then concentrated in vacuo and purified by column chromatography on silica gel (AcOEt ? 5% MeOH/AcOEt, then 90% DCM/MeOH) to give the product as a brown semi-solid. The solid was further purified by trituration with ice cold iPr2O ether to give the product as an off white solid, which was used without further purification (3.00 g, 22%). LC-MS: Rt = 2.31 min; [M+H]+ 259/261.

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 89182-17-2, 6-Chloro-3,4-pyridinediamine.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel (Prof. Dr.); Falcenberg, Mathias (Dr.); EP2818472; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 107504-08-5 , The common heterocyclic compound, 107504-08-5, name is 5-Fluoro-2-picolinic acid, molecular formula is C6H4FNO2, 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 suspension of the aniline compound 1-3 (0.17 g, 0.57 mmol) and 0.104 g (0.74 mmol) of 5-fluoropyridine-2-carboxylic acid in 5 mL of dichloromethane were added 0.289 g (1.14 mmol) of BOPC1 and 0.22 g (1.7 mmol) of diiosopropylethylamine. The solution was stirred at room temperature for 40 min, and quenched with water (10 mL). The mixture was extracted with two 30 mL portions of dichloromethane. The combined organic extracts were concentrated; the residue was purified by flash chromatography (12 g of Si02: 0 to 4% MeOH in CH2C12 plus 1% NH4OH) to give a free base, which was treated with HCl in ether to form the salt l-4a (0.192 g, 74%). LCMS for l-4a (conditions A): tR = 1.94 min, m/e = 423 (M+H).

The synthetic route of 107504-08-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WU, Wen-Lian; BURNETT, Duane A.; STAMFORD, Andrew W.; CUMMING, Jared N.; BENNETT, Chad Edward; GILBERT, Eric J.; PENG, Xuanjia; SCOTT, Jack D.; YU, Younong; WO2012/139425; (2012); 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.113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.0061, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Bromonicotinaldehyde

To a mixture of 5-bromopyridine-3-carbaldehyde (XXXVIII) (6.00 g, 32.26 mmol, 1.0 eq), 3,3-difluoropyrrolidine (5.56 g, 38.71 mmol, 1.20 eq) and TEA (5.39 mL, 38.71 mmol, 1.2 eq) in DCE (200 mL) was stirred at room temperature for 30 mm, then added sodium triacetoxyborohydride (10.25 g, 48.38 mmol, 1.50 eq) in one portion at room temperature under N2. The mixture was stirred at room temperature for 6 h. TLC showed the reaction was complete. The reaction was quenched with iN NaOH (100 mL), extracted with DCE (100 mL x 2). The combined organic layers were washed with brine (100 mL), dried and concentrated. The residue was purified by silica gel chromatography (column height: 50 mm, diameter: 50 mm, 300-400 mesh silica gel, DCMIMeOH=3 0/1 -*20/1) to give 3 -bromo-5 -((3,3 -difluoropyrrolidin- 1- yl)methyl)pyridine (XL): Yellow oil (8.00 g, 28.9 mmol, 89.5% yield). ?H NMR (CDC13, 400 MHz) ppm 2.30 (spt, J=7.2Hz. 2H), 2.75 (t, J=6.8Hz, 2H), 2.91 (t, J13.2Hz, 2H), 7.85 (s, 1H), 8.45 (s, 1H), 8.59 (d, J=2Hz, 1H); ESIMS found for C,0H,,BrF2N2 m/z 277.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-81-3, 5-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (271 pag.)WO2017/24026; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 76469-41-5, 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. 76469-41-5, name is 2,3,5-Trifluoropyridine, molecular formula is C5H2F3N, 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 1(R)-(trans-(1-carbamoyl-4-adamantyl)) 3-(3,5-difluoropyridin-2-yloxy)pyrrolidine-1- carboxylateStep 1; To a stirred solution of (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate(1.1O g, 5.89 mmol) and 2,3,5-trifluoropyridine (0.86 g, 6.48 mmol) in dry THF (20 ml.) and dry DMF (4 ml_), at rt was added 60% NaH in oil (0.35 g, 8.84 mmol). The mixture was stirred in a 40 0C oil bath overnight, cooled to rt, diluted with ether (175 ml_), washed with water (25 mL) and brine (25 ml_), and dried over Na2SO4.Removal of the solvent left a dark oil (1.94 g) which was purified by chromatography on a 40-g silica cartridge eluted with a 0 – 100% EtOAc in hexanes gradient to afford (R)-tert-butyl 3-(3,5-difluoropyridin-2-yloxy)pyrrolidine-1- carboxylate (0.83 g, 47%). LC-MS Method 1 tR = 1.85 min, m/z = 301.

According to the analysis of related databases, 76469-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; LEFTHERIS, Katerina; SINGH, Suresh, B.; TICE, Colin, M.; YE, Yuanjie; ZHUANG, Linghang; WO2010/141424; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1003-73-2, 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. 1003-73-2, name is 3-Methylpyridine 1-oxide, molecular formula is C6H7NO, 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.

Into the flask, 300 g of methylene chloride and 50 g of 3-picoline-N-oxide were added and the mixture was stirred and cooled to 5°C at a constant pressure.A dropping funnel was charged with a mixed solution of 240 g of 2,4,6-triisopropyl-3-benzoyl chloride and 200 g of methylene chloride and slowly added dropwise to the dichloromethane mixture of 3-picoline-N-oxide. In the dropping process, the reaction temperature is controlled at 5 to 10°C.The addition was completed within about 3 hours. The reaction was incubated for 2 hours and then warmed to 40°C overnight.After the end of the reaction, cool down to 5 ~ 10 °C, slowly add 200g of water, after desolvation steam distillation, collecting 100 ~At 102°C/760mmHg, the distillate was extracted with methylene chloride. After the aqueous layer was separated, 57.4 g of product was de-solvated.The content of 2-chloro-5-methylpyridine was 98percent, 2-chloro-3-methylpyridine was 0.5percent, and the yield of 2-chloro-5-methylpyridine was 96.2percent.

According to the analysis of related databases, 1003-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Hong Sun Biochemical Co., Ltd.; Chen Honglong; Mu Dengyou; Xue Yi; Chen Xinchun; Zhong Jingsong; Wang Fujun; Yang Cheng; (5 pag.)CN107721912; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 110860-92-9, 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. 110860-92-9, name is 5,6-Dichloropyridin-3-ol. A new synthetic method of this compound is introduced below.

Sodium acetate (4.Og, 49.38mmoI) was added to a mixture of 5,6-dichloropyridin-3-ol (8g, 49.38mmol), Pd(OAc)2 (1.43g, 6.41 mmol) and Pd(dppf)C12 DCM complex (5.23g, 6.4lmmol) in EtOH (lOOmL) in an autoclave. The autoclave was filled with CO gas (22Opsi) and stirred at 90C for 6 h. The reaction mass was cooled to RT, excess gas evacuated in vacuo and the reaction mass was filtered through a celite bed. It was washed with EtOAc and the clear filtrate was concentrated under reduced pressure. Theresidue was purified by CC (0-40% EtOAc in PE) and the pure fractions were concentrated to get ethyl 3- chloro-5-hydroxypicolinate (9.2g, 93%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,110860-92-9, 5,6-Dichloropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 139022-27-8, 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 139022-27-8 as follows.

Example 166-fluoro-3-iodo-imidazo^ ,2-alpha]pydine (29)As shown in Fig. 5, 6-Fluoro-3-iodo-imidazo[1 ,2-alpha]pyridine (29) was prepared according to a literature procedure (Enguehard et al., J. Org. Chem. 65: 6572-6575 (2000), incorporated herein by reference in its entirety). N-iodosuccinimide (9.2g, 40.8 mmol) was added to a solution of 6-fluoro-imidazo[1 ,2-alpha]pyridine 26 (Example 15) (7.6g, 40.8 mmol) in dry acetonitrile (100 ml.) at O0C. The reaction was warmed to room temperature and then stirred for 12 hours. The mixture was filtered and the cake washed with acetonitrile and water and dried under high vacuum to afford 6-fluoro-3-iodo-imidazo[1 ,2-alpha]pyridine 29 off white solid. 8.5 g, 88% yield.1H NMR (300 MHz, CDCI3, 297K) delta 7.14 (td, J = 2.1 , 7.8 Hz, 1 H), 7.59 (dd, J = 5.1 , 9.9 Hz, 1 H), 7.72 (s, 1 H), 8.07 (distorted t, J = 3.0 Hz, 1 H).ESI MS (MeOH) calcd for C7H4FIN2 262.03, found m/z (M++1 ) 263.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,139022-27-8, its application will become more common.

Reference:
Patent; ISIS INNOVATION LTD.; EBETINO, Frank, Hallock; MAZUR, Adam; LUNDY, Mark, Walden; RUSSELL, Robert, Graham Goodwin; WO2010/33978; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 272-52-6 ,Some common heterocyclic compound, 272-52-6, molecular formula is C6H5N3, 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.

Into a vessel was placed a solution comprising 1.0 g of lH-pyrazolo[4,3- b]pyridine (Exp-l-gl, 8.4 mmol) in 12 mL of MeOH/H20 (1 : 1, vol). Into the solution was added dropwise a solution of Br2 ( 1.6 g, 10 mmol) in MeOH/H20 (1 : 1, 5 mL) maintaining the solution temperature at 0 C during the addition. The reaction mixture thus prepared was stirred at this temperature for 40 min. The resulting precipitate was collected by filtration and the filter cake thus obtained was neutralized with saturated Na2C03 solution. The neutralized precipitate was filtered, washed with water and dried in vacuum. The crude product thus obtained (Exp-l-g2,1.2 g, 71 %) was used for the next step directly without purification. The identity of the product was verified by proton NMR in accordance with the procedures set forth above. 1HNMR: (400 MHz, DMSO) delta 13.66 (br, 1H), 8.55 (d, 1H, J = 4.0 Hz), 8.03 (dd, 1H, J = 8.8 Hz, 1.2 Hz), 7.42-7.45 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,272-52-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; JONES, Philip; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/63100; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem