Day: March 3, 2022

Reference of 6515-09-9, 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. 6515-09-9, name is 2,3,6-Trichloropyridine. A new synthetic method of this compound is introduced below.

General procedure: Complex (1 .71 mol%) and 3 mL of stock solution (made from 3.333g TCP A in IPA 30 mL) are added to each reactor, followed by NEt3 (446 pL). The reactors are purged with nitrogen (3 times) and hydrogen (3 times) then hydrogenated at 0.5 MPa and 85 C for 180 mm in a Biotage Endeavor. 40 pL aliquot of each reaction mixture is added to 1 mL MeCN and analysed by normal HPLC method.HPLC areas are converted to concentration (pmol/mL) from the gradients equations in the multipoint external standard.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6515-09-9, 2,3,6-Trichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; JOHNSON MATTHEY PUBLIC LIMITED COMPANY; MORTIMER, Danny Lee; (19 pag.)WO2017/85476; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 38186-84-4, 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. 38186-84-4, name is 2-Chloro-5-fluoro-3-picoline, molecular formula is C6H5ClFN, 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.

To a solution of 2-chloro-5-fluoro-3-methylpyridine D38 (0.50 g, 2.82 mmol) in dry toluene (12.5 ml) were added sodium t-butoxyde (0.462 g, 4.81 mmol), Pd2(dba)3 (0.315 g, 0.344 mmol), BINAP (0.642 g, 1.031 mmol) and benzophenone imine (0.692 ml, 4.12 mmol). The resulting mixture was degassed (3×pump/N2) and then heated to 80 C. After 1 h stirring, the mixture was cooled down to room temperature, diluted with Et2O (400 ml) and filtered through a celite pad. Volatiles were evaporated, the resulting oil was dissolved in THF (34 ml) and HCl (1.408 ml of a 2 M aqueous solution, 2.82 mmol) was added. The mixture was stirred at room temperature for 1.5 h, then neutralized with a saturated NaHCO3 aqueous solution and diluted with DCM (200 ml). The inorganic layer was back-extracted with DCM (2×50 ml). The collected organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (Biotage SP4 12M, Cy/EtOAc 60/40). Collected fractions gave the title compound D39 (0.20 g, 1.554 mmol, 55.2% yield from D38, two steps), as an orange solid. MS: (ES/+) m/z: 127 (M+1). C6H7FN2 requires 126.1H NMR (400 MHz, DMSO-d6) delta(ppm): 7.73 (d, 1H), 7.23 (dd, 1H), 5.60 (bs, 2H), 2.04 (s, 3H).

According to the analysis of related databases, 38186-84-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
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 21948-75-4, 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. 21948-75-4, name is 2-(Methylsulfinyl)pyridine, molecular formula is C6H7NOS, 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.

General procedure: p-NO2DPPA (91.3 mg, 0.25 mmol) and DABCO (28.0 mg, 0.25 mmol) were added to a solution of the sulfoxide (0.10 mmol) in toluene (0.35 mL). After stirring for 2 h at reflux, the mixture was diluted with AcOEt/n-hexane (1:5) (30 mL). Then, the mixture was washed with saturated aqueous NaHCO3 (25 mL) and brine (25 mL), and dried over Na2SO4. Concentration of the solvent in vacuo followed by purification of the residue on a silica gel column (AcOEt:n-Hexane 1:5-0:1) gave the desired alpha-azido sulfide.

According to the analysis of related databases, 21948-75-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ishihara, Kotaro; Shioiri, Takayuki; Matsugi, Masato; Tetrahedron Letters; vol. 58; 41; (2017); p. 3932 – 3935;,
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

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.1256789-09-9, name is Methyl 6-chloro-2,4-dimethylnicotinate, molecular formula is C9H10ClNO2, molecular weight is 199.6342, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl 6-chloro-2,4-dimethylnicotinate

This mixture was dissolved in dioxane (10 ml) and added at 0 C. to a solution prepared by dissolving 594 mg (25.8 mmol) sodium in MeOH (11 ml) at 0 C. This reaction mixture was stirred at RT for 3 h. Then the reaction solution was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue again a mixture of 6-chloro-4-(methoxymethyl)-2-methyl-pyridine-3-carboxylic acid methylester and 6-chloro-2-(methoxymethyl)-4-methyl-pyridine-3-carboxylic acid methylester was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256789-09-9, Methyl 6-chloro-2,4-dimethylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Grunenthal GmbH; US2012/101079; (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

Electric Literature of 1064783-29-4, 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.1064783-29-4, name is 5-Chloro-3-fluoro-2-nitropyridine, molecular formula is C5H2ClFN2O2, molecular weight is 176.53, as common compound, the synthetic route is as follows.

Example 4(c) 6-chloro-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol: In a 30 mL scintillation vial equipped with a stir bar was added ethyl acetate (10 mL), 5-chloro-3-fluoro-2-nitropyridine (101 mg, 0.56 mmol), and 3-aminopentane (74 mL, 0.63 mmol). The reaction was stirred at room temperature until starting material was consumed (TLC 25% ethyl acetate in hexanes). To this solution was added tin(II) chloride dihydrate (560 mg, 2.5 mmol), and the mixture was stirred until the aryl nitro was completely reduced (4 h to overnight). The solution was transferred from the scintillation vial to a 5 mL microwave tube, followed by the addition of carbonyldiimidazole (>10 equiv). The reaction was heated in a microwave reactor at 150 C. for 20 min. After cooling, water was added, and the organic layer was separated, concentrated, and purified by flash chromatography over silica gel (30-40% ethyl acetate in hexanes) to give 6-chloro-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol (93 mg, 0.390 mmol, 68% yield).

Statistics shows that 1064783-29-4 is playing an increasingly important role. we look forward to future research findings about 5-Chloro-3-fluoro-2-nitropyridine.

Reference:
Patent; Collibee, Scott; Lu, Pu-Ping; Ashcraft, Luke W.; Browne, William F.; Garard, Marc Andrew; Morgan, Bradley P.; Morgans, David J.; Bergnes, Gustave; Muci, Alex; US2008/242695; (2008); 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. 52559-11-2, name is Pyridine-2,3,4-triamine, the common compound, a new synthetic route is introduced below. Computed Properties of C5H8N4

10. 6-(8-Amino-pyrido[2, S-typyrazinS-ytyS-trifluoromethyl-nicotinamide Dissolve 2,3,4-triaminopyridine (8 mmol) in water (20 mL). Add NaHCO3 (2.1 g, 25 mmol), dioxane (25 mL) and 6-(2-bromo-acetyl-5-trifluoromethyl)-nicotinamide (8 mmol), and stir at 100C for 4 hours. Cool the mixture and extract with EtOAc (4 x 10 mL). Wash the combined organic extracts with brine and dry over Na2SO4. Purify the residue by preparative HPLC to give the title compound.

The synthetic route of 52559-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/42289; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22282-99-1, 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.22282-99-1, name is 4-Bromo-2-methylpyridine, molecular formula is C6H6BrN, molecular weight is 172.02, as common compound, the synthetic route is as follows.

To a stirred solution of 4-bromo-2- methylpyridine (3 g, 17.44 mmol) and diethyl carbonate (2.75 ml, 22.67 mmol) in THF (30 ml)was added LDA (4mL) (2M in THF/hept/ethylbenzene) at -78C. The solution was stirred for 1 h prior to the addition of another portion of LDA (4.00 mL). Stirring was continued at -70C for one more hour and then the reaction was quenched by the addition of water. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried (Na2504). The solvent was evaporated and the residue was purified byflash columnchromatography on silica gel (0-100% EtOAc in Hex) to give the title compound. LC/MS =245.75 [M+lj

The chemical industry reduces the impact on the environment during synthesis 22282-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LIM, Yeon-Hee; XU, Jiayi; ZHOU, Wei; (123 pag.)WO2017/74833; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem