Day: March 18, 2021

Electric Literature of 84539-30-0, 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. 84539-30-0, name is 5-Bromo-N-methylpyridin-2-amine, molecular formula is C6H7BrN2, 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.

NaHMDS (1 M, 12 mL) was added slowly to a mixture of 5-bromo-2-(N-methylamino)pyridine (2.0 g, 10.7 mmol) and (Boc)2O (2.8 g, 12.8 mmol, 3.0 mL) in THF (20 mL) at 0 C under N2. The resulting mixture was allowed to warm to 20 C and stirred for 13 hours. TLC (petroleum ether / ethyl acetate = 3/1) showed trace amount of compound 64 and a major new spot with lower polarity. The mixture was quenched with sat. NaHCO3 (30 mL) and extracted with EtOAc (50 mL x 2). The organic layers were combined, washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give a residue. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 10/1 to 3/1) to give 5-bromo-2-(N-methyl-N-(t-butoxycarbonyl)amino)pyridine (2.8 g, 91% yield) as a light yellow liquid. 1H NMR 400 MHz CDCl3 8.40 – 8.39 (m, 1H), 7.71 – 7.65 (m, 2H), 3.37 (s, 3H), 1.49 (s, 9H). ESI-MS (m/z): 287.0 (M+H)+.

According to the analysis of related databases, 84539-30-0, 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

Synthetic Route of 5470-70-2, Adding some certain compound to certain chemical reactions, such as: 5470-70-2, name is Methyl 6-methylnicotinate,molecular formula is C8H9NO2, 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 5470-70-2.

A solution of methyl 6-methylnicotinate (0.5 g, 3.3 mmol) in THF (16 mL) at 0¡ã C. was treated dropwise with lithium aluminum hydride in THF (6.6 mL, 1 M), stirred at 0¡ã C. for 1.5 hours, treated with ethyl acetate (3 mL), stirred at 25¡ã C. The reaction was partitioned between ethyl acetate and saturated NaHCO3, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the residue (0.395 g) in dichloromethane (16 mL) was treated with MnO2 (2 g), stirred at 25¡ã C. for 68 hours, filtered through celite.(R). to give the title compound (0.326 g, 80percent yield), which was used without further purification.

According to the analysis of related databases, 5470-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 942947-94-6 ,Some common heterocyclic compound, 942947-94-6, molecular formula is C5H4BrClN2, 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.

Production Example 23-1 tert-Butyl N-(5-bromo-4-chloropyridin-2-yl)-N-[(tert-butoxy)carbonyl]carbamate To a solution of 5-bromo-4-chloropyridin-2-amine (3.0 g, 14 mmol), di-tert-butyl dicarbonate (9.5 g, 43 mmol), and triethylamine (6.1 mL, 43 mmol) in tetrahydrofuran (100 mL), 4-dimethylaminopyridine (0.18 g, 1.5 mmol) was added, and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and then the residue was separated and purified by silica gel column chromatography (ethyl acetate:heptane) to obtain the title compound (3.2 g, 55% yield). 1H-NMR Spectrum (400 MHz, CDCl3) delta (ppm): 1.48 (s, 18H), 7.47 (s, 1H), 8.58 (s, 1H).

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. 942947-94-6, 5-Bromo-4-chloropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Lt.d; Tanaka, Keigo; Fukuyama, Takashi; Murai, Norio; Itano, Wataru; Hirota, Shinsuke; Iida, Daisuke; Azuma, Hiroshi; (32 pag.)US2016/168176; (2016); 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 67443-38-3, name is 5-Bromo-2-chloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Bromo-2-chloro-3-nitropyridine

To a cooled solvent of MeOH (50.0 mL) was added Na (2.90 g, 126.4 mmol) portion-wise, then the mixture was warmed to rt and stirred until Na was all dissolved, then the solution was added to a suspension of 5-bromo-2-chloro-3-nitropyridine (10.0 g, 42.12 mmol, Shanghai long sheng hua gong, china) in MeOH (100 mL) at 0 C. The reaction mixture was stirred at 0 C. for 1 hour, then warmed up to rt and stirred further for 16 hours, then concentrated to 80 mL and quenched with water (100 mL). The precipitate was filtered, washed with water (50 mL*2) and dried under infrared light to give the title compound as a pale yellow solid (9.62 g, 98%). MS (ESI, pos. ion) m/z: 233.0 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 67443-38-3.

Reference:
Patent; Calitor Sciences, LLC; Xi, Ning; US2014/134133; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 115170-40-6, 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. 115170-40-6, name is 5-Bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H7BrN2, 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 125 Step 1: (2,3-dihydro-lH-pyrrolo[2,3-b]pyridin-5-yl)boronic acid and 5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-2,3-dihydro-lH-pyrrolo[2,3-b]pyridine To a stirred solution of 5-bromo-2,3-dihydro-lH-pyrrolo[2,3-b]pyridine (100 mg, 0.50 mmol) and 1 ,2-dimethoxyethane (4 mL) in a microwave vial equipped with a stirbar was added bis(pinacolato diborane) (175 mg, 0.65 mmol), potassium acetate (148 mg, 1.5 mmol) and 1,1′- bis(diphenylphosphino)ferrocene-palladium(II)dichloride (20.9 mg, 0.025 mmol). The mixture was purged with nitrogen gas for 5 min and the reaction mixture was stirred at 90 C for 5.5 h. The reaction mixture was filtered through a celite bed and washed with dichlorome thane (10 mL). The filtrate was concentrated to dryness in vacuo affording a crude mixture of (2,3-dihydro-lH- pyrrolo[2,3-b]pyridin-5-yl)boronic acid and 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2,3- dihydro-lH-pyrrolo[2,3-b]pyridine used for the next step without any further purification.

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 115170-40-6, 5-Bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1597-32-6, 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 1597-32-6, name is 2-Amino-6-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

NBS (50. Og, 280.99mmol) was added slowly to 6-fluoropyridin-2-amine (30g, 267.61mmol) in MeCN (300mL) cooled to 10-20C over a period of 30 minutes. The resulting solution was stirred at ambient temperature for 60 minutes then the solvent removed under reduced pressure. The residue was diluted with water, the precipitate collected by filtration, washed with water (200mL) and dried under vacuum to afford the desired material (50. Og, 98%) as a white solid, which was used without further purification. NMR Spectrum: 1H MR (300MHz, DMSO-d6) delta 6.29 (1H, d), 6.57 (2H, bs), 7.65 (1H, t). Mass Spectrum: m/z (ES+)[M+H]+ = 191.

According to the analysis of related databases, 1597-32-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARLAAM, Bernard Christophe; PIKE, Kurt Gordon; WO2015/170081; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 64119-42-2, 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. 64119-42-2, name is Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate, molecular formula is C10H9ClN2O2, 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.

(d) l-[3 -Cyano-5-(ethoxycarbonyl) -6-methylpyridine -2-yI] azetidinc -3-carboxylic acid; Ethyl 6-chloro-5-cyano-2-methylnicotinate (50.98 g, 227 mmol), azetidine-3-carboxylic acid (24.09 g, 238 mmol) and DIPEA (118.9 mL, 681 mmol) were suspended in EtOH (250 mL) and heated at reflux for 1 h. The reaction mixture was cooled to r.t and added drop- wise to KH5O4 (154.5 g, 1135 mmol) in water (3000 mL). The solids were collected by filtration and dried under vacuum to afford 1-[3-Cyano-5-(ethoxycarbonyl)-6-methylpyridine-2- yl]azetidine-3-carboxylic acid as a solid, which was used without further purification. Yield: 65.33 g (100%). 1H NMR (400 MHz, CDCl3): 6 1.37 (3H, t, J= 7.1 Hz), 2.72 (3H, s), 3.59-3.68 (1H, m), 4.31 (2H, q, J= 7.1 Hz), 4.55-4.68 (4H, m), 8.28 (1H, s). M5 m/z: 290 (M+l).

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 64119-42-2, Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate.

Reference:
Patent; ASTRAZENECA AB; WO2006/73361; (2006); 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. 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C7H5BrN2

Example 42 Synthesis of 8-[3-(2-methoxy-pyrimidin-5-yl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinoline 43 Step-1 Preparation of 8-(3-bromo-pyrrolo[2,3-b]pyridine-1-sulfonyl)-quinoline 44 Into a round bottom flask was added 3-bromo-7-azaindole (3, 1.18 g, 5.99 mmol) and tetra-N-butylammonium bromide (193 mg, 0.600 mmol), and 5.0 M sodium hydroxide (15.4 mL). 8-Quinoline-sulfonyl chloride (1.64 g, 7.19 mmol) in dichloromethane (5.9 mL) was added dropwise at room temperature. After a few hours, all starting materials were gone. After 30 mL of dichlormethane was added, two layers were separated. The aqueous layer was washed with dichloromethane. The combined organic layers were washed with 1 M sodium bicarbonate, water, and brine and dried over anhydrous sodium sulfate. The crude material was concentrated under reduced pressure and was purified by column chromatography (55-80% ethyl acetate in hexane) to yield the desired product as a light yellow colored solid (44, 1.72 g, 4.43 mmol). MS(ESI) [M+H+]+=389.4.

The synthetic route of 74420-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ibrahim, Prabha N.; Bremer, Ryan; Gillette, Sam; Cho, Hanna; Nespi, Marika; Mamo, Shumeye; Zhang, Chao; Artis, Dean R.; Lee, Byunghun; Zuckerman, Rebecca; US2006/100218; (2006); 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. 86873-60-1, name is 5-Chloro-2-picolinic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Chloro-2-picolinic acid

Step 3A. (?)-Methyl 2-(5-chloropicolinamido)-9-methyl-6,7-dihydro-5H- benzo[7]annulene-8-carboxylateTo a solution of 5-chloropicolinic acid (354 mg, 2.248 mmol) in dichloromethane (5 mL) was added HATU (940 mg, 2.473 mmol) and DIPEA (0.589 mL, 3.37 mmol). After stirring for 10 min, methyl 2-amino-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8- carboxylate from preparation J, step Jl (260 mg, 1.124 mmol) was added. The mixture was stirred at rt for 4 h. Ethyl acetate (100 mL) was added and the organic layer was washed with water. After concentration of the organic layer, the residue was purified using silica gel column chromatography (hexanes-100% EtOAc) to give methyl 2-(5- chloropicolinamido)-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate (345 mg, 0.930 mmol, 83 % yield). LCMS (M+H)+ = 371.3. XH NMR (400 MHz, chloroform-if) delta 9.84 (s, IH), 8.56 (dd, J=2.4, 0.6 Hz, IH), 8.25 (dd, J=8.4, 0.6 Hz, IH), 7.88 (dd, J=8.4, 2.4 Hz, IH), 7.73 (d, J=2.3 Hz, IH), 7.63 (dd, J=8.0, 2.3 Hz, IH), 7.20 (d, J=8.3 Hz, IH), 3.82 (s, 3H), 2.55 (t, J=6.5 Hz, 2H), 2.44 (s, 3H), 2.18 – 2.08 (m, 4H).

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, 86873-60-1, 5-Chloro-2-picolinic acid.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; THOMPSON III, Lorin A.; SHI, Jianliang; WU, Yong-Jin; MARCIN, Lawrence R.; RAJAMANI, Ramkumar; HIGGINS, Mendi A.; WO2012/162330; (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.52313-50-5, name is Picolinimidamide, molecular formula is C6H7N3, molecular weight is 121.14, as common compound, the synthetic route is as follows.COA of Formula: C6H7N3

Intermediate 108: ethyl 6-hvdroxy-2-(2-pyridinyl)-4-pyrimidinecarboxylateDiethyl 2-oxobutanedioate (4.31 mL, 26.6 mmol)(TCI Europe) was added to a suspension of 2- pyridinecarboximidamide (4.19 g, 26.6 mmol)(Alfa Aesar) in Ethanol (130 mL) at r.t. under nitrogen. Triethylamine (7.41 mL, 53.1 mmol) was added dropwise and the reaction mixture heated to 80 C and stirred for 24 h in total. The reaction was allowed to cool to r.t. and concentrated in vacuo to a black oil. The crude product was purified by column chromatography using a 0 to 100% solution of 20% MeOH in DCM/DCM to give the title product as a brown oil (2.91 g, 45% yield) which was used in the subsequent reaction without further purification.LCMS (Method A): Rt = 0.69 min, MH+ = 246.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52313-50-5, Picolinimidamide, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Stephen John; BARKER, Michael David; CAMPBELL, Matthew; HUMPHREYS, Philip; LIDDLE, John; SHEPPARD, Robert John; WILSON, David; WO2012/52390; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem