Category: 885276-93-7

Electric Literature of 885276-93-7, 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. 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate, molecular formula is C10H9BrN2O2, 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: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40% aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.

According to the analysis of related databases, 885276-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C10H9BrN2O2

Ethyl 5 -bromopyrazolo [1,5 -a]pyridine-3 -carboxylate (0.100 g, 0.372 mmol), 1- methyl-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrazole (0.101 g, 0.483mmol) and XPhos-Pd G3 (7.9 mg, 9.3 jimol) were placed in a pressure vial. The reaction mixture was degassed (3x vacuumlAr), then THF (2 mL) and potassium phosphate tribasic (0.5 M aq.) (1.12 mL, 0.557 mmol) were added. The reaction mixture was degassed again, and stirred at 100 C for 1 h. Solvent was removed under reduced pressure. The obtained residue was dissolved in MeOH (1.0 mL)/THF (1.0 mL), and LiOH (1 M aq.) (1 .12 mL, 1.12 mmol) was added. The reaction mixture was stirred under microwave irradiation at 120 C for 15 mm. The mixture was acidified with TFA, the solvent was removed under reduced pressure, the residue was purified by preparativeHPLC to afford Intermediate 39 (0.055 g, 61% yield) as an off-white solid. MS(ESI) m/z:243.0 (M+H) ?H NMR (500MHz, DMSO-d6) oe ppm 8.81 (dd, J=7.2, 0.8 Hz, 1H), 8.43(s, 1H), 8.33 (s, 1H), 8.10 (dd,J=1.9, 0.8 Hz, 1H), 8.05 (s, 1H), 7.36 (dd,J=7.3, 2.1 Hz,1H), 3.90 (s, 3H).

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, 885276-93-7, Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 885276-93-7, Adding some certain compound to certain chemical reactions, such as: 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate,molecular formula is C10H9BrN2O2, 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 885276-93-7.

Synthesis of Exemplary CompoundsSynthesis of ethyl 5-{{2R,4S)-4-fluoro-2-(3-fluoroDhenyl)Dyrrolidin-1-yl)Dyrazolo[1 ,5- -3-carboxylate (X- 1)[000300] A N2 purged flask was charged with ethyl 5-bromopyrazolo[1 ,5-a]pyridine-3- carboxylate (27 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (2 mg, 2 muiotaetaomicronIota), xantphos (5 mg, 8 muiotaetaomicronIota), cesium carbonate (46 mg, 0.14 mmol), 1 ,4-dioxane (0.5 ml_) and (2R,4S)-4-fluoro-2-(3-fluorophenyl)pyrrolidine (1-6) (18 mg, 0.1 mmol). The contents were heated to 120 C for 12 hours. Upon cooling to room temperature the reaction was partitioned with EtOAc and water. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude product was purified by column chromatography on silica gel withEtOAc/hexanes gradient as eluant to yield ethyl 5-((2R,4S)-4-fluoro-2-(3- fluorophenyl)pyrrolidin-1 -yl)pyrazolo[1 ,5-a]pyridine-3-carboxylate (X-1 ). 1 H NMR (400MHz, CDCI3) delta 8.20 (s, 1 H), 8.16 (d, J = 7.6 Hz, 1 H), 7.31 (td, J = 5.6, 7.6 Hz, 1 H), 7.05 (d, J = 7.6 Hz, 1 H), 6.98 (d, J = 2.8 Hz, 1 H), 6.96 – 6.91 (m, 2 H), 6.24 (dd, J = 2.8, 8.0 Hz, 1 H), 5.39 (d, J = 52.8 Hz, 1 H), 5.04 (dd, J = 7.2, 9.2 Hz, 1 H), 4.34 – 4.26 (m, 2 H), 4.17 – 3.90 (m, 2 H), 2.93 – 2.81 (m, 1 H), 2.1 1 (dddd, J = 3.6, 9.2, 13.2, 40.8 Hz, 1 H). MS m/z 372.1 (M+1 )+.

According to the analysis of related databases, 885276-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; MOLTENI, Valentina; FAN, Yi; LOREN, Jon; SMITH, Jeffrey M.; FLATT, Brenton T.; WO2012/116217; (2012); 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. 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. Safety of Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate

A solution of ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate (240 mg, 0.89 mmol) in 40% H2SO4 (12 mL) was stirred at 100 C. for 4 hours, then cooled to rt, and neutralized to pH=7 with aq. NaOH (6 M) in ice bath. The resulted mixture was extracted with DCM (25 mL×2). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a light yellow solid (175 mg, 99.5%). MS (ESI, pos. ion) m/z: 196.9 [M+H]+.

The synthetic route of 885276-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; Xi, Ning; US2014/234254; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 885276-93-7 ,Some common heterocyclic compound, 885276-93-7, molecular formula is C10H9BrN2O2, 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.

Synthesis of fR)-ethyl 5-(2-(3-cvano-5-fluoroDhenyl)-4A-difluoroDyrrolidin-1- yl)pyrazolo[1,5-alpyridine-3-carboxylate (X-8)[000304] A N2 purged flask was charged with ethyl 5-bromopyrazolo[1 ,5-a]pyridine-3- carboxylate (100 mg, 0.37 mmol), palladium acetate (1 .7 mg, 7 muiotaetaomicronIota), xantphos (7 mg, 1 1 muiotaetaomicronIota), cesium carbonate (170 mg, 0.52 mmol), 1 ,4-dioxane (0.5 ml_) and (R)-3- (4,4-difluoropyrrolidin-2-yl)-5-fluorobenzonitrile (I-24) (84 mg, 0.37 mmol). The contents were heated to 140 C for 1 hour under microwave irradiation. Upon cooling to room temperature the reaction was partitioned with EtOAc and water. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude product was purified by column chromatography on silica gel with EtOAc/hexanes gradient as eluant to yield (R)-ethyl 5-(2-(3-cyano-5- fluorophenyl)-4,4-difluoropyrrolidin-1 -yl)pyrazolo[1 ,5-a]pyridine-3-carboxylate (X-8). 1 H NMR (400MHz, CDCI3) delta 8.26 (d, J = 7.6 Hz, 1 H), 8.24 (s, 1 H), 7.38 (s, 1 H), 7.33 – 7.29 (m, 1 H), 7.25 -7.21 (m, 1 H), 6.93 (d, J = 2.8 Hz, 1 H), 6.19 (dd, J = 2.8, 7.6 Hz, 1 H), 5.14 (dd, J = 4.4, 9.2 Hz, 1 H), 4.34 – 4.25 (m, 2 H), 4.25 – 4.16 (m, 1 H), 4.05 – 3.93 (m, 1 H), 3.14 – 2.98 (m, 1 H), 2.53 – 2.42 (m, 1 H), 1 .34 (t, J = 7.2 Hz, 3 H). MS m/z 415.1 (M+1 )+.

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. 885276-93-7, Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; MOLTENI, Valentina; FAN, Yi; LOREN, Jon; SMITH, Jeffrey M.; FLATT, Brenton T.; WO2012/116217; (2012); 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 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate

A colorless mixture of A-13 (900.0 mg, 3.34 mmol) in H2504 (50%,10.0 mL) was stirred at 120 C for 3 hours. The mixture was diluted with ice-water, neutralizedwith solid Na2CO3 to pH = 7, and extracted with DCM (50 mL x 2). The combined organiclayers were washed with brine (10 mL), dried over Na2504, filtered and concentrated to affordA-14 (550.00 mg, 2.79 mmol) as an oil. ?H NMR (400 MHz, CDC13) oe11 8.38 – 8.32 (m, 1H),7.95 (d, 1H), 7.72 (d, 1H), 6.83 (dd, 1H), 6.47 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 885276-93-7.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 885276-93-7, 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. 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate. A new synthetic method of this compound is introduced below.

Synthesis of 5-bromo-N, N-bis(4-methoxybenzyl)pyrazolo[ 1 , 5-a]pyridine-3-carboxamide-26)1-25 1-26[000270] To a suspensions of ethyl 5-bromopyrazolo[1 ,5-a]pyridine-3-carboxylate (0.27 g, 1 .0 mmol) in EtOH (5 ml_) was added 6 N KOH (0.3 uL, 2.0 mmol). The reaction was heated to reflux for 3 hours then cooled to room temperature and neutralized to pH 6 with 1 M HCI. The resulting solid was filtered and dried under vacuum to yield 5-bromopyrazolo[1 ,5-a]pyridine-3-carboxylic acid (I-25) as a white solid. 1 H NMR (400MHz, DMSO-c/6) delta 8.83 (d, J = 7.6 Hz, 1 H), 8.42 (s, 1 H), 8.21 (d, J = 2.4 Hz, 1 H), 7.30 (dd, J = 2.0, 7.6 Hz, 1 H). MS m/z 240.9, 242.9 (M+1 )+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,885276-93-7, its application will become more common.

Reference:
Patent; IRM LLC; MOLTENI, Valentina; FAN, Yi; LOREN, Jon; SMITH, Jeffrey M.; FLATT, Brenton T.; WO2012/116217; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem