Day: April 14, 2022

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 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromo-7-methylimidazo[1,2-a]pyridine

To a solution of 6-bromo-7-methylimidazo[1 ,2-a]pyridine (100 mg, 0.47 mmol) in CH2CI2 (1 mL), was added 1-lodopyrrolidine-2,5-dione (84 mg, 0.47 mmol) and MeOH (0.1 mL). The resulting mixturewas stirred at room temperature for 2 h. The reaction was poured into water and extracted with ethyl acetate. The organic phase was dried over Na2504, filtered, and concentrated in vacuo. The residue was purified by SiC2 column chromatography (hexane/EtOAc = 1:1) to give 122 mg (77 %) of the product as a white solid. LC/MS m/z: 337.00 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 116355-18-1.

Reference:
Patent; ARISAN THERAPEUTICS INC.; PLEWE, Michael; BROWN, Eric; GANTLA, Vidyasagar; HENKEL, Gregory; MCCORMACK, Kenneth; SOKOLOVA, Nadzeda V.; SHIN, Young-Jun; (147 pag.)WO2018/13430; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 139585-48-1, name is 2-Chloro-5-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 139585-48-1

a) 5′-Methoxy-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester To a stirred solution of piperidine-4-carboxylic acid ethyl ester (0.52 g, 3.34 mmol) and 2-chloro-5-methoxy-pyridine in 10 mL of toluene was added (13 mg, 0.057 mmol) of Pd(II) acetate, (17 mg, 0.027 mmol) of BINAP and tBuOK (0.44 g, 3.90 mmol). The mixture was heated at 120 C. for two hours, concentrated under vacuo and the residue was directly purified on column chromatography (SiO2, EtOAc/Hept 1:2) yielding 0.17 g (24%) of the title compound as a light yellow oil. ES-MS m/e: 265.3 (M-41′).

With the rapid development of chemical substances, we look forward to future research findings about 139585-48-1.

Reference:
Patent; Jablonski, Philippe; Knust, Henner; Nettekoven, Matthias; Patiny-Adam, Angelique; Ratni, Hasane; Riemer, Claus; US2011/53948; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52311-50-9, 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. 52311-50-9, name is 2-Chloro-4-ethoxypyridine, molecular formula is C7H8ClNO, 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.

6.01.22.02 1-(4-ethoxy-pyridin-2-yl)-piperazine hydrochloride 860 mg piperazine was added to 350 mg 2-chloro-4-ethoxy-pyridine in 3.5 mL n-butanol. The reaction was stirred 1.5 days at 115 C. The reaction was filtered and the filtrate was washed with water and evaporated. 1N HCl was added to the residue and the precpipate was filtered to give 238 mg of the desired product. Rt: 0.3 min (method B), (M+H)+: 208

According to the analysis of related databases, 52311-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; US2013/184248; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22282-99-1 , The common heterocyclic compound, 22282-99-1, name is 4-Bromo-2-methylpyridine, molecular formula is C6H6BrN, 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-bromo-2-methyl-pyridine (2.00 g, 11.6 mmol, CAS 22282-99- 1) and diethyl carbonate (1.65 g, 13.9 mmol, 1.68 mL) in THF (15.0 mL) was added LDA (2 M, 11.63 mL) at -60 C dropwise. Then the mixture was stirred at -60 C for 2 hours. On completion, the reaction mixture was quenched by addition of saturated ammonium chloride solution 30 mL at 0 C, and extracted with ethyl acetate 60 mL (3 X 20 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether:ethyl acetate = 20:1 to 8:1) to give the title compound (1.30 g, 46% yield) as a yellow oil.1H NMR (400MHz, CDCl3) delta = 8.40 (d, J = 5.2 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.40 (dd, J = 1.6, 5.2 Hz, 1H), 4.21 (q, J = 7.2 Hz, 2H), 3.83 (s, 2H), 1.29 (t, J = 7.2 Hz, 3H).

The synthetic route of 22282-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3222-50-2, 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. 3222-50-2, name is 4-Methylnicotinic acid. A new synthetic method of this compound is introduced below.

General procedure: Into a 1L open reactor was added 500g of carboxylic acid raw material (chemically pure) and stirring was turned on (600 r/min) from the reactorThe bottom is continuously fed with ammonia gas (chemical purity, water content of 5.1% by weight, flow rate of 100 g/min) to the carboxylic acid feed. After the reaction was allowed to proceed for TC hours at the reaction temperature TA, ammonia gas flow was stopped. The contents of the reactor were sampled and subjected to nuclear magnetic proton and elemental analysis to characterize the amide intermediate. Specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3, Table A-4, Table A-5 and Table A-6. These characterization results show that the amide intermediates obtained have an extremely high purity (above 99%).In this embodiment, the ammonia gas can be directly replaced with waste ammonia gas (from Yangzi Petrochemical Plant, containing approximately50wt% of ammonia gas, the rest were toluene, oxygen, nitrogen, steam, carbon monoxide, and carbon dioxide, and the flow rate of this waste ammonia was 130g/min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3222-50-2, 4-Methylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Sinopec Yangzi Petrochemical Co., Ltd.; Sinopec Corporation; Sun Hailong; Wei Yanyu; Gao Yilong; Chen Xinhua; Miao Jun; Li Na; Kan Lin; Bai Jiye; Chen Shaohui; Yang Aiwu; Xu Yuexing; (76 pag.)CN104557357; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58327-75-6, Adding some certain compound to certain chemical reactions, such as: 58327-75-6, name is 3-Aminothieno[2,3-b]pyridine-2-carboxylic acid,molecular formula is C8H6N2O2S, 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 58327-75-6.

General procedure: To the solution of appropriate 2-aminobenzoic acid in dried THF or 1,4- dioxane was added triphosgene (0.35 eq). The mixture was stirred under reflux for 4-8 hrs. Then the solvent was removed in vacuo to give the isotaic anhydride as a solid in theoretical yield. 1H NMR indicated the product was of sufficient purity and was used in the next step without further purification.

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. 58327-75-6, 3-Aminothieno[2,3-b]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Huang, Guozheng; Roos, Dominika; Stadtmueller, Patricia; Decker, Michael; Tetrahedron Letters; vol. 55; 26; (2014); p. 3607 – 3609;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 169205-95-2, 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. 169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine. A new synthetic method of this compound is introduced below.

Example 17 Production of 6-(oxazolo[4,5-b]pyridin-2-ylamino)-N-(2,6-diisopropylphenyl)hexanamide 2-Methylthiooxazolo[4,5-b]pyridine (65.0 mg, 0.39 mmol) and 6-amino-N-(2,6-diisopropylphenyl)hexanamide (114 mg, 0.39 mmol) were mixed together and stirred at 90 C. for 2 hours. The reaction mixture was purified by preparative thin layer chromatography (elution solvents: hexane_acetone=5:3). The resulting crude crystal was recrystallized from dichloromethane-ether-hexane, to recover the objective compound as a colorless needle-like crystal. Melting Point: 152-153 C. IR (KBr) cm-1: 3416, 2964, 1656, 1571, 1413. 1H-NMR (d6-DMSO) delta: 1.11 (12H, d, J=6.8 Hz), 1.43-1.57 (2H, m), 1.64-1.77 (4H, m), 2.35 (2H, t, J=7.3 Hz), 3.08 (2H, sept, J=6.8 Hz), 3.38 (2H, dd, J=12.9, 6.8 Hz), 6.89 (1H, dd, J=7.8, 5.1 Hz), 7.09 (1H, d, J=8.3 Hz), 7.09 (1H, d, J=7.1 Hz), 7.19 (1H, dd, J=8.3, 7.1 Hz), 7.53 (1H, dd, J=7.8, 1.5 Hz), 7.87 (1H, br s), 8.06 (1H, dd, J=5.1, 1.5 Hz), 8.65 (1H, br s). EIMS m/z (relative intensity): 408 (M+, 100). Elementary Analysis: C24H32N4O2 Required: C, 70.56; H, 7.89; N, 13.71. Found: C, 70.70; H, 7.87; N, 13.51.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,169205-95-2, its application will become more common.

Reference:
Patent; Kowa Company, Ltd.; US6362208; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1227594-89-9, 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. 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, molecular formula is C6H3F4NO, 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.

[00602] Step A: A solution of triphenylphosphine (1.34 g, 5.1 mmol) in THF (25 mL) was cooled to 0 C and treated with DIAD (1.0 mL, 5.12 mmol). The mixture was stirred for 15 min, then tert-butyl (3-bromo-1-((1r,4r)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate (1.5 g, 3.41 mmol) was added as a solid, followed by a solution of 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (1.24 g, 6.83 mmol) in THF (10 mL) over 5 min. The mixture was allowed to warm slowly to room temperature overnight. The mixture was partitioned between water (100 mL) and EtOAc (100 mL) and the aqueous layer was extracted with EtOAc (2 x 30 mL). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (10-40% EtOAc/hexanes) to afford tert-butyl (3-bromo-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate (1.07 g, 52 % yield).

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 1227594-89-9, 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13269-19-7, 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. 13269-19-7, name is 2-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 2-nitropyridin-3-amine (4 g, 28.8 mmol) in AcOH (40 mL) was added potassium acetate (2.82 g, 28.8 mmol) and the mixture stirred for 1 h at room temperature. Br2 (1.481 mL, 28.8 mmol) was added slowly to the reactionmixture and the mixture stirred at room temperature for 16 h. The solid formed wascollected by vacuum filtration, washed with diethyl ether (2×10 mL) and dried underhigh vacuum to afford 4-bromo-2-nitropyridin-3-amine (6 g, 27.5 mmol, 96% yield) as a yellow solid. LCMS (ESI)m/e 218.0 [(M+H), calcd for C5H5BrN3O2 218.01; LC/MS retention time (method B): tR = 0.61 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13269-19-7, 2-Nitropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1142363-52-7, 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. 1142363-52-7, name is JNJ-40346527, molecular formula is C27H35N5O2, 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 31 4-Cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide sulfate salt A suspension of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (24.8 mg, 0.0537 mmol), as prepared in Example 15, in acetonitrile (1.0 mL) was heated to yield a solution. To the solution was added a solution of concentrated sulfuric acid (0.0062 mL) in water (0.5 mL) at room temperature. The solution was reduced via evaporation with flowing nitrogen gas (approximately 1.0 mL). The solution was then allowed to sit overnight at room temperature in a sealed vial. The resulting crystals were then collected via filtration and air-dried. The white solid was characterized by Powder X-Ray Diffraction (PXRD), Differential Scanning Calorimetry (DSC), Thremogravimetric Analysis (TGA), and single-crystal X-ray diffraction. The DSC for the sulfate salt showed a 241 degree Celsius endotherm maximum. The PXRD of the sulfate salt product is shown in and the prominent peaks are shown in the table below. Representative 2-Theta peaks of the sulfate salt product are shown below:

According to the analysis of related databases, 1142363-52-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Illig, Carl R.; Chen, Jinsheng; Meegalia, Sanath K.; Wall, Mark J.; US2009/105296; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem