Month: April 2022

Electric Literature of 700811-29-6, 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 700811-29-6 as follows.

Step 2: 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde To a solution of 1-(2-chlorophenyl)ethanone (1.08 mL, 8.36 mmol) in AcOH (33 mL) was added 2-chloro-4-hydrazinopyridine (1.20 g, 8.36 mmol). The reaction mixture was allowed to stir at rt for 1 h and was then diluted with water. A white precipitate formed, and the mixture was extracted with EtOAc several times. The organic solutions were combined, washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated.The residue was dissolved in DMF (15 mL) and added to a solution of phosphoryl chloride (1.56 mL, 16.7 mmol) in DMF (13 mL) which had been stirring at rt for 30 min. The reaction mixture was allowed to stir at 80 C. for 18 h and then at rt for 35 h. The mixture was diluted with water and extracted several times with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-(2-chlorophenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-4-carbaldehyde (1.95 g, 73%). LCMS (AA): m/z=318 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,700811-29-6, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Chau, Ryan W.; Cullis, Courtney A.; Duffey, Matthew O.; Gipson, Krista E.; Hu, Yongbo; Li, Gang; Sintchak, Michael D.; Vos, Tricia J.; US2013/165464; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 102645-33-0, Adding some certain compound to certain chemical reactions, such as: 102645-33-0, name is 2,5-Dichloroisonicotinaldehyde,molecular formula is C6H3Cl2NO, 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 102645-33-0.

(2) To be equipped with mechanical stirring, thermometer,After nitrogen substitution in the three-port reaction flask of the constant pressure dropping funnel,Add the raw materials 4a-1 (200mmol) in sequence,500.0ml tetrahydrofuran, start stirring, and cool down to -85 -90 ,Add 2mol / L n-butyllithium (210mmol) dropwise,The temperature during the dropping is maintained at -85 -90 , and the temperature is kept for 1h after the dropping is completed.A solution of the raw material 2,5-dichloropyridine-4-aldehyde (200 mmol) + 140.0 ml of tetrahydrofuran was added dropwise.After the dropwise addition, the temperature was kept for 0.5h, and the temperature was naturally raised to room temperature for 3h.The reaction solution was poured into 10% aqueous ammonium chloride solution, and extracted with 320.0 ml of toluene,Separate the liquid and extract the aqueous phase once with 320.0 ml of toluene,Combine the organic phases, wash twice with 260.0 ml of water, and separate.The organic phase is dried by adding 12g of anhydrous sodium sulfate and filtered,The organic phase is concentrated (-0.08 -0.09MPa, 55 65 ) to no avail,Add 150.0ml petroleum ether and stir for 0.5h, filter, rinse the filter cake with petroleum ether,Intermediate 4a-2 (150 mmol) was obtained with a yield of 75%.

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. 102645-33-0, 2,5-Dichloroisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanxi Laite Optoelectric Materials Co., Ltd.; Wu Xingzhi; Xue Zhen; Wang Jinping; (49 pag.)CN111004237; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 823221-95-0, 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. 823221-95-0, name is 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Step 2: To a solution of 5-chloro-4-iodo-2-(trifluoromethyl)pyridine (18.2 g, 59.2 mmol) in diethylether (200 mL), at -78 C in a 1L 3 neck RBF, was added n-butyl lithium (1.6 M in hexane, 44.5 mL, 71.1 mmol). The resulting solution was stirred at that temperature for 10 minutes and ethyl-N-Boc-(S)-pyroglutamate (16.75 g, 65.2 mmol) in diethylether (130 mL) was added slowly, and the resulting solution was stirred at that temperature for 1 h. The reaction was stopped by the addition of saturated NH4C1 solution (150 mL) and extracted with EtOAc (2 x 250 mL).The organic layer was washed with water (2 x 150 mL), dried over anhydrous Na2S04 and concentrated to yield ethyl (S)-2-((tert-butoxycarbonyl)amino)-5-(5-chloro-2- (trifluoromethyl)pyridin-4-yl)-5-oxopentanoate which was carried forward to the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823221-95-0, 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; SHAO, Pengcheng Patrick; KRIKORIAN, Arto, D.; VACHAL, Petr; WO2015/17302; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To a mixture of 2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetic acid (34, 0.899 g, 3.21 mmol) in ethyl acetate (20 ml) was added 5-(trifluoromethyl)pyridin-3-amine (10, 0.520 g, 3.21 mmol), triethylamine (1.0 ml) and propylphosphonic anhydride (50 wt % solution in ethyl acetate, 2.51 ml, 4.22 mmol). The mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was suspended in a mixture of ethyl acetate and hexane. The solid precipitate was collected by filtration and washed with hexane. After drying, this provided 1.03 g of compound 46. MS ESI [M+H+]+=425.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Plexxikon Inc.; Lin, Jack; Ibrahim, Prabha N.; Albers, Aaron; Buell, John; Guo, Zuojun; Pham, Phuongly; Powers, Hannah; Shi, Songyuan; Spevak, Wayne; Wu, Guoxian; Zhang, Jiazhong; Zhang, Ying; (132 pag.)US2017/267660; (2017); A1;,
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 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