Month: March 2022

Reference of 73112-16-0, 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 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : 2,6-dibromo-4-methylpyridine (300 mg, 1.20 mmol), tert-butyl carbamate (168 mg, 1.44 mmol), sodium ie/t-butoxide (138 mg, 1.44 mmol) and l,l’-bis(di-tert- butylphosphino)ferrocene palladium dichloride (39.0 mg, 0.06 mmol) were dissolved in nitrogen sparged 2-MeTHF. The system was evacuated and purged with nitrogen (3X) then placed into 70C oil bath. After 3 hours, the temperature was increased to 80C for 4 hours. The reaction mixture was diluted with EtOAc and brine. The product was extracted with EtOAc, washed with brine, dried and concentrated under reduced pressure to afford crude iert-butyl {4-methyl-6- [(trimethylsilyl)ethynyl]pyridin-2-yl} carbamate. Copper (I) iodide (0.13 g, 0.7 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.24 g, 0.35 mmol) were added to the crude product and then dissolved in nitrogen sparged dimethylacetamide. The system was evacuated and purged with nitrogen (3X). Triethylamine (1.5 mL, 10.45 mmol) and trimethylsilylactylene (1.5 mL, 10.45 mmol) were added and the solution was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (25 mL) and brine. The product was extracted with EtOAc (25 mL), washed with brine, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (5% EtOAc). The fractions were concentrated under reduced pressure, suspended in hexanes, filtered in vacuo and dried to afford iert-butyl {4-methyl-6-[(trimethylsilyl)ethynyl]pyridin-2-yl} carbamate. MS ESI calcd. for Ci6H25N202Si [M + H]+ 305, found 305.

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 73112-16-0, 2,6-Dibromo-4-methylpyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michelle R.; ROMEO, Eric T.; KATTAR, Solomon D.; CHRISTOPHER, Matthew; ALTMAN, Michael D.; NORTHRUP, Alan B.; ELLIS, John Michael; BOYLE, Brendan O’; DONOFRIO, Anthony; GRIMM, Jonathan; REUTERSHAN, Michael H.; CHILDERS, Kaleen Konrad; OTTE, Ryan D.; CASH, Brandon; DUCHARME, Yves; HAIDLE, Andrew M.; SPENCER, Kerrie; VITHARANA, Dilrukshi; WU, Lingyun; ZHANG, Li; ZHANG, Peng; BEAULIEU, Christian; GUAY, Daniel; WO2014/48065; (2014); 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. 175204-82-7, name is Methyl 4-(trifluoromethyl)nicotinate. A new synthetic method of this compound is introduced below., SDS of cas: 175204-82-7

3-Isopropyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (Table 1, No. 81) 2 g of methyl 4-trifluoromethylnicotinate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0 C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of two hours and stirring was then continued at this temperature until the reaction, according to TLC, had ended. The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil. 1H-NMR (CDCl3, 300 MHz): d 1.41 (d, J 6.9 Hz, 6H), 3.22 (m, 1H), 7.78 (d, J=5 Hz 1H), 9.02 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

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, 175204-82-7, Methyl 4-(trifluoromethyl)nicotinate.

Reference:
Patent; Harmsen, Sven; Bastiaans, Henricus Maria Martinus; Schaper, Wolfgang; Tiebes, Jorg; Doller, Uwe; Jans, Daniela; Sanft, Ulrich; Hempel, Lta Waltraud; Thonessen, Di. Maria-Theresia; Taapken, Thomas; Rook, Burkhard; Kern, Manfred; US2003/162812; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-88-9 ,Some common heterocyclic compound, 153034-88-9, molecular formula is C6H5ClIN, 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 2-chloro-4-iodo-3-methylpyridine (303 mg, 1.20 mmol) (Aldrich, catNo.724092), phenylboronic acid (160 mg, 1.32 mmol) (Aldrich, catNo.78181) and sodium carbonate (317 mg, 2.99 mmol) in tert-butyl alcohol (10 mL) and water (6 mL) was added Pd-127 (181 mg, 0.239 mmol). The resulting mixture was purged with N2, and then heated at 80 C. for 2 h. The reaction mixture was diluted with methylene chloride, washed with saturated NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on a silica gel column eluting with 10 to 20% ethyl acetate in hexanes to give the desired product (225 mg, 92%). LCMS calculated for C12H11ClN (M+H)+: m/z=204.2; found 204.2.

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. 153034-88-9, 2-Chloro-4-iodo-3-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Li, Zhenwu; Wu, Liangxing; Yao, Wenqing; (48 pag.)US2017/320875; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, the common compound, a new synthetic route is introduced below. Quality Control of 2-Methoxy-4,6-dimethylnicotinonitrile

To a cooled (ice water bath) solution of 2-methoxy-4,6-dimethylnicotinonitrile (10 g, 61.7 mmol) in Et2O (200 mL) was added dropwise 1 M LiAIH4 in Et2O (123 mL, 123 mmol). The ice bath was removed and the reaction mixture was stirred at r.t. for 16 h. The reaction mixture was cooled in an ice water bath and quenched with a mininum amount of water (until no more hydrogen was generated). The reaction was filtered and the insoluble material was washed with 10: 1 DCM/MeOH. The combined organic filtrates were concentrated. The residue was purified via column chromatography (0 – 30% MeOH/DCM; 100 g-HP- silica gel column) to give (2-methoxy-4,6-dimethylpyridin-3- yl)methanamine (8.9 g) as a yellowish semi-solid.

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BRACKLEY, III, James A.; GRAVES, III, Alan Peterson; KNIGHT, Steven David; MCNULTY, Kenneth C.; NEWLANDER, Kenneth Allen; TIAN, Xinrong; (114 pag.)WO2017/2064; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine, molecular formula is C6H7BrN2O, 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. COA of Formula: C6H7BrN2O

[00210] To a stirred solution of triphosgene (1 eq, 0.83 mmol) in DCM (16 ml_) at -20 C and under an atmosphere of N2 was added a solution of 2-bromo-6-methoxy-pyridin-4- ylamine (1 eq, 0.83 mmol) in DCM (6 ml_) followed by triethylamine (2.5 eq, 2.08 mmol). The reaction was stirred at -20 C for 15 mins then allowed to warm to RT and stirred at RT for 30 mins. The reaction was cooled to -20 C and a solution of ((1S,3R)-(3-amino-cyclopentyl)- carbamic acid benzyl ester in dry DCM (3 ml_) was added and the reaction stirred at -20 C for 15 mins then at RT for 90mins. More triethylamine (2 eq, 1.66 mmol) was added and the reaction was at RT for 1 h. The reaction was quenched with methanol and concentrated in vacuo. The crude was purified by column chromatography to benzyl N-[(1S,3R)-3-[(2-bromo- 6-methoxy-4-pyridyl)carbamoylamino]cyclopentyl]carbamate (311 mg, 81 %) as a light yellow gum. AnalpH2_MeOH_4min, Rt: 3.21 min; m/z 463/465[M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 1196152-34-7.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; RABBITTS, Terrence; QUEVEDO, Camilo; CRUZ, Abimael; PHILIPS, Simon; FALLON, Philip Spencer; DUNN, Jonathan Neil; FREEM, Joshua Robert; LEE, Lydia Yuen-Wah; TRAORE, Tenin; WILLIAMS, Sophie Caroline; (219 pag.)WO2019/145718; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 912369-42-7, 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 912369-42-7, name is Methyl 3-((tert-butoxycarbonyl)amino)picolinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 3-{[(tert-butoxy)carbonyl]amino}pyridine-2-carboxylate (1.53 g, 6.06 mmol) was dissolved in AcOH (30 mL). PtO2 (770 mg) was added and the mixture was stirred under H2 atmosphere (5 bar) for 12 hours. The catalyst was filtered off, the solvent was evaporated and the residue taken up with DCM (50mL) and washed with NaHCO3 aqueous saturated solution. The organic phase was concentrated to give methyl 3-{[(tert-butoxy)carbonyl]amino}piperidine-2- carboxylate (1.42 g, 91 % yield) as diastereoisomeric mixture.

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 912369-42-7, Methyl 3-((tert-butoxycarbonyl)amino)picolinate.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, 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. Product Details of 1111637-94-5

Example B-6: Preparation of (2S)-1-(4-(3-(2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-isopropyl- 1 H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-6)B-6-1 B-6-2 B-6-3Preparation of 5-bromo-3-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-2)B-6-1 B-6-2 To a solution of 5-bromo-3-methyl-1 H-pyrrolo[2,3-b]pyridine (B-6-1 ) (1.2 g, 5.68 mmol) in THF (30 mL) was added NaH (0.34 g, 8.5 mmol) under N2 at O0C, 4-bromophenylsulfonyl chloride (1.2 g, 6.8 mmol) was added 30 minutes later. The mixture was stirred at room temperature for 1.5 h. TLC (Petroleum ether: EtOAc = 5:1 ) showed that the reaction was complete. Saturated aqueous NaCI (10 mL) was added, and the mixture was filtered to give 5-bromo-3-methyl-1-(phenylsulfonyl)-1 H-pyrrolo[2,3-b]pyridine (B-6-2) (0.8 g) as a white solid. The organic layer was separated from the filtrate, concentrated to 8 mL, then filtered to give 5-bromo-1-(4-bromophenylsulfonyl)-3-methyl-1 H-pyrrolo[2,3-b]pyridine (0.5 g). Two batches were combined to give 5-bromo-3-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-6-2) (1.3 g, 65.2%) as a white solid.

With the rapid development of chemical substances, we look forward to future research findings about 1111637-94-5.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1532517-95-5, 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. 1532517-95-5, name is 5-Bromo-3-fluoro-2-nitropyridine. A new synthetic method of this compound is introduced below.

A solution of 5-bromo-3-fluoro-2-nitropyridine (400 mg, 1.81 mmol) and 2-methoxyethanamine (408 mg, 5.43 mmol) in tetrahydrofuran (10 mL) was stirred at 25 C. for 2 hours, whereupon it was diluted with ethyl acetate (100 mL) and washed with water (50 mL). The organic layer was washed with saturated aqueous sodium chloride solution (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford C18 as a yellow solid. Yield: 430 mg, 1.56 mmol, 86%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1532517-95-5, 5-Bromo-3-fluoro-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; Aspnes, Gary Erik; Bagley, Scott W.; Curto, John M.; Edmonds, David James; Flanagan, Mark E.; Futatsugi, Kentaro; Griffith, David A.; Huard, Kim; Lian, Yajing; Limberakis, Chris; Londregan, Allyn T.; Mathiowetz, Alan M.; Piotrowski, David W.; Ruggeri, Roger B.; (127 pag.)US2019/382384; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58481-17-7, 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 58481-17-7, name is Methyl 2-(hydroxymethyl)isonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-(hydroxymethyl)isonicotinate (8.36 g, 50 mmol) was dissolved in dichloromethane (150 ml_). Dess-Martin periodinane (25 g, 58.94 mmol) was added and the mixture stirred at room temperature for 2 h 30 min. Sodium sulfothioate (59.3 g, 375.00 mmol) was dissolved in satd NaHCO3 and added to the reaction mixture. The suspension was vigorously stirred at room temperature for 15 min, DCM was added and the phases were separated. The aqueous phase was extracted with DCM twice and the combined organic layers were dried over MgSO and evaporated. The residue was purified by automated flash chromatography on a Biotage KP-SIL 340g column. Gradient heptanes / EtOAc 80:20 to 65:35 over 5 CV was used as mobile phase. Methyl 2-formylisonicotinate (7 g, 85 %) was isolated as an off-white solid. 1H NMR (400 MHz, cdcl3) delta 4.00 (s, 3H), 8.09 (dd, 1 H), 8.49 (s, 1 H), 8.95 (d, 1 H), 10.15 (s, 1 H). MS m/z 165 (M+H)+

According to the analysis of related databases, 58481-17-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; CHENG, Leifeng; SCHELL, Peter; WO2012/47156; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 856851-48-4, 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 856851-48-4 as follows.

Hydrogen peroxide-urea complex (31 .04 g, 330 mmol) was added in one portion to a solution of 2-chloro-5-ethoxypyridine (26.0 g, 1 65 mmol) in dichloromethane (250 mL) at 0 00 then trifluoroaceticanhydride (62.4 g, 297 mmol, 41 .3 0 mL) was added dropwise. The mixture was stirred at 20 00 for 16 h. The reaction mixture was quenched by addition of saturated aqueous sodium thiosulfate (150 mL). The mixture was extracted with dichloromethane (200 mL x 3), then the combined organic phases were washed with saturated aqueous sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give a crude residue that was purified by chromatography (silica, petroleumether : ethyl acetate 1:0 to 1:2) to give 2-chloro-5-ethoxypyridine 1-oxide (22.0 g, 126.7 mmol, 77%) as a yellow solid. 1H NMR (400 MHz, ODd3) O 8.05 (d, J2.6 Hz, 1 H), 7.29 (d, J9.0 Hz, 1 H), 6.81 (dd, J2.6, 9.1 Hz, 1 H), 3.97 (q, J6.9 Hz, 2H), 1 .37 (t, J7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,856851-48-4, its application will become more common.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem