Category: 74420-15-8

Reference of 74420-15-8, 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. 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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.

[0393] 3-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine: [0394] 3-bromo-lH-pyrrolo[2,3-b]pyridine (10.7 kg, 54.3 moles) was added to 94.3 kg of THF in a 200 L glass-lined reactor. The solid was dissolved completely by stirring. After the mixture was cooled to about 10-15 C, NaH (3.4 kg, 85 moles) was added in portions (about 200-250 g each portion) every 3 to 5 minutes while venting any gas released by the reaction. After the addition of NaH, the mixture was stirred for one hour while maintaining the temperature of about 10-20 C. 4-methylbenzenesulfonylchloride (12.4 kg, 65.0 moles) was added at a rate of 0.5 kg/10 minutes at about 10-20 C. After the addition was complete, the temperature was maintained at about 10-20 C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-lH-pyrrolo[2,3-b]pyridine was less than 1% (after about 1.5 hours). Typical retention time for 3-bromo-l-tosyl-lH-pyrrolo[2,3- bjpyridine was 20.2 minutes. [0395] The reaction was quenched with water (10.7 kg) while maintaining the temperature below 20 C. Dichloromethane (41.3 kg) was added to the mixture. Then 3% HC1 acid (42.8 kg) was added into the mixture while maintaining the temperature below 25 C. After the addition, the phases were allowed to separate for 0.5 hour. The aqueous phase was extracted twice with dichloromethane. During each extraction, the mixture was stirred for 15 minutes and then held for 15 minutes. All the organic phases were combined. The combined organic phases were washed with 3% HC1 acid (33.4 kg) and water (40 kg). During each wash, the mixture was stirred for 15 minutes and then held for 30 minutes. [0396] The mixture was transferred into a 50 L vacuum filter and filtered through silica gel (3 kg). The cake was washed with dichloromethane (35 kg) twice. The filtrate and washings were combined. The organic phase was concentrated below 40 C under vacuum of a pressure less than -0.085 MPa until 10 L mixture remained. Petroleum ether (9 kg) was added into the residue. The mixture was stirred until it was homogeneous. The slurry was transferred into a 50 L vacuum filter and filtered. The cake was washed with petroleum ether (9 kg). A light brown solid resulted (17 kg, 99.7% purity as measured by HPLC analysis (method A), 94% yield of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine).

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 74420-15-8, 3-Bromo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HOOCK, Thomas Carl; CHAVAN, Ajit Bhiwaji; CHEN, Yingxue; GARG, Varun; HUANG, Jiayin; MAHNKE, Lisa Ann; ROBERTSON, Sarah Marie; SEWELL, Kathryn Lea; TAYLOR, Lori Kell; WO2014/201332; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74420-15-8, 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. 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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.

22.0 g (111.66 mmol) of the intermediate product (A) is dissolved in 350 ml of THF, and n-BuLi (49.13 mL, 122.82 mmol) is slowly added at -78 C. After 1 hour, TsCl (25.55 g, 133.99 mmol) was added and stirred for 4 hours under a stream of nitrogen

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 74420-15-8, 3-Bromo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; Cheil Industries Co., Ltd.; Hong, Jin Suk; Yu, Dong Gyu; Yu, Uhn Sun; Lee, Han Ir; Kang, Dong Min; Lee, Sang Sin; Jang, Yuna; Jung, Su Young; Han, Su Jin; (31 pag.)KR2015/15252; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 74420-15-8, 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 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A. 3-Bromo-1H-pyrrolo[2,3-b]pyridine and ammonia (0.5M in 1,4-dioxane) is heated to reflux. After 5 h the solution is concentrated. The residue is chromatographed on a silica gel plug to give 1H-pyrrolo[2,3-b]pyridin-3-ylamine.

According to the analysis of related databases, 74420-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 74420-15-8, 3-Bromo-1H-pyrrolo[2,3-b]pyridine, 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, Product Details of 74420-15-8, blongs to pyridine-derivatives compound. Product Details of 74420-15-8

[0383] Example lb: 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (7a) [0384] 3-bromo-lH-pyrrolo[2,3-b]pyridine (6a) (10.7 kg, 54.3 moles) was added to 94.3 kg of THF in a 200 L glass-lined reactor. The solid was dissolved completely by stirring. After the mixture was cooled to about 10-15 C, NaH (3.4 kg, 85 moles) was added in portions (about 200-250 g each portion) every 3 to 5 minutes while venting any H2 gas released by the reaction. After the addition of NaH, the mixture was stirred for one hour while maintaining the temperature of about 10-20 C. 4-methylbenzenesulfonylchloride (12.4 kg, 65.0 moles) was added at a rate of 0.5 kg/10 minutes at about 10-20 C. After the addition was complete, the temperature was maintained at about 10-20 C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-lH-pyrrolo[2,3- bjpyridine (6a) was less than 1% (after about 1.5 hours). [0385] The reaction was quenched with water (10.7 kg) while maintaining the temperature below 20 C. Dichloromethane (41.3 kg) was added to the mixture. Then 3% HC1 (42.8 kg) was added into the mixture while maintaining the temperature below 25 C. After the addition, the phases were allowed to separate for 0.5 hour. The aqueous phase was extracted twice with dichloromethane. During each extraction, the mixture was stirred for 15 minutes and then held for 15 minutes. All the organic phases were combined. The combined organic phases were washed with 3% HC1 (33.4 kg) and water (40 kg). During each wash, the mixture was stirred for 15 minutes and then held for 30 minutes. [0386] The mixture was transferred into a 50 L vacuum filter and filtered through silica gel (3 kg). The cake was washed with dichloromethane (35 kg) twice. The filtrate and washings were combined. The organic phase was concentrated below 40 C under vacuum of a pressure less than -0.085 MPa until 10 L mixture remained. Petroleum ether (9kg) was added into the residue. The mixture was stirred until it was homogeneous. The slurry was transferred into a 50 L vacuum filter and filtered. The cake was washed with petroleum ether (9 kg). A light brown solid resulted (17 kg, 99.7% purity as measured by HPLC analysis (method A), 94% yield of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (7a)).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; TANOURY, Gerald, J.; JUNG, Young, Chun; MAGDZIAK, Derek; LOOKER, Adam; WO2013/6634; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 74420-15-8 ,Some common heterocyclic compound, 74420-15-8, molecular formula is C7H5BrN2, 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.

[0193] In a microwave tube was placed ethyl 2-bromothiazole-4-carboxylate (944 mg, 4 mmol), 3-bromo-1H-pyrrolo[2,3-blpyridine (867 mg, 4.40 mmol), and K2C03 (663 mg, 4.80 mmol). The tube was sealed and DMSO (7.5 ml) was added. The mixture was heated at 150C for 3 h. The mixture was poured into EtOAc/H20 (30 mL/30 mL). The organic was dried (Na2504) and filtered. After removal of the solvent, the product was purified (twice) by silica gel chromatography using 10-20% EtOAc/hexane as the eluent to give ethyl 2-(3- bromo- 1 H-pyrrolo[2,3 -blpyridin- 1 -yl)thiazole-4-carboxylate (587 mg, 1.667 mmol, 41.7% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74420-15-8, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74420-15-8, 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. 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

Example 1G3-Bromo-1-(phenylsulfonyl)-1H-pynolo[2,3-b]pyridineTo a 0 C. solution of EXAMPLE 1F (25 g, 127 mmol) in N,N-dimethylformamide (200 mL) was slowly added sodium hydride (3.37 g, 133 mmol) over several minutes. After stirring for 30 minutes in the cold water bath, benzenesulfonyl chloride (17.18 ml, 133 mmol) was added via a syringe. The solution was allowed to warm to room temperature overnight, quenched slowly with 500 mL water, stirred for 30 minutes, and then filtered. The solid obtained was washed with water, followed by 300 mL of hexanes, dried over high-vacuum for 16 hours to give the title compound which was used without further purification. MS (ESL) m/z 338.7 (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,74420-15-8, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; US2011/257187; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74420-15-8, Adding some certain compound to certain chemical reactions, such as: 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine,molecular formula is C7H5BrN2, 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 74420-15-8.

Example 79 Synthesis of (2-Ethoxy-naphthalen-1-yl)-[3-(4-methanesulfonyl-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-methanone 84 Step 1-Preparation of (3-Bromo-pyrrolo[2,3-b]pyridin-1-yl)-(2-ethoxy-naphthalen-1-yl)-methanone 85 3-Bromo-7-azaindole (500 mg, 2.0 mmol) 3 was dissolved in N,N-dimethylformamide (50 mL) and sodium hydride (210 mg, 5.3 mmol, 60% dispersion in mineral oil) and 2-Ethoxy-naphthalene-1-carbonyl chloride (710 mg, 3.0 mmol) were added. The reaction mixture was stirred at ambient temperature for 30 min, cast into ice water (100 mL) and extracted into ethyl acetate. The organic portion was dried with anhydrous magnesium sulfate, filtered and the filtrate concentrated. Purification via column chromatography (10% Ethyl acetate in hexanes) provided the desired product 85 (800 mg, 80%).

According to the analysis of related databases, 74420-15-8, the application of this compound in the production field has become more and more popular.

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

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 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Bromo-1H-pyrrolo[2,3-b]pyridine

To a mixture of tert-butyl piperazine- 1-carboxylate (224 mg, 1.2 equiv.), 3-bromo-lH- pyrrolo[2,3-£]pyridine (197 mg, 1 equiv.), RuPhos (9.3 mg, 0.02 equiv.) and Ruphos Pd Gl, MTBE adduct (16.3 mg, 0.02 equiv.) in THF (2 mL), under argon atmosphere, a 1.3 M THF solution of LiHMDS (1.92 mL, 2.5 equiv.) was added. The resulting mixture was purged with argon for 5 min, and was then sealed in a vial and heated at 70 C for 3 h. The reaction mixture was cooled to RT, quenched by an addition of 1 M HC1 (1.5 mL), diluted with EtOAc and poured into a sat. solution of sodium bicarbonate. After extracting with 3 portions of EtO Ac, combined organic extracts were dried, and the solvent was removed in vacuo. The obtained residue was purified by flash chromatography on silica gel (eluting with a cyclohexane/EtOAc gradient, 0-100 % of EtO Ac) to afford the expected product (165 mg). LCMS: MW (calc’d): 302.4; MS (ES+, m/z): 303.2 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 74420-15-8.

Reference:
Patent; E-THERAPEUTICS PLC; JURKOVIC, Mihaela; LANDEK, Ivana Ozimec; POLJAK, Tanja; RO?CIC, Maja; STUBBERFIELD, Colin; VADLAMUDI, Srinivasamurthy; (228 pag.)WO2019/43372; (2019); 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

Adding a certain compound to certain chemical reactions, such as: 74420-15-8, 3-Bromo-1H-pyrrolo[2,3-b]pyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

General procedure: In a dry and argon flushed 10 mL Schlenk tube, equipped with a magnetic stirring bar and a septum, Pd(O2CCF3)2 (7 mg, 2 mol%) was dissolvedin anhydrous THF (1 mL). Then, SPhos (16 mg, 4 mol%) was added and the reaction mixture was stirred at r.t. for 10 min, beforethe 3-bromo-7-azaindole (9a; 158 mg, 0.8 mmol, 1.0 equiv) and the previously zincated ester derivative 6 (1.3 mmol, 1.6 equiv) were added subsequently. The mixture was stirred at 50 C for the indicated time. The completion of the reaction was checked by GC analysis of reaction aliquots quenched with H2O (0.5 mL). The mixture was then quenched with a sat. aq NH4Cl (3 mL) and extracted with EtOAc(3 ¡Á 10 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude products 4a and 4b were purifiedby flash chromatography

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

Reference:
Article; Barl, Nadja M.; Malakhov, Vladimir; Mathes, Christian; Lustenberger, Philipp; Knochel, Paul; Synthesis; vol. 47; 5; (2015); p. 692 – 700;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem