Day: July 30, 2021

Synthetic Route of 98198-48-2, 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. 98198-48-2, name is 2-Amino-5-bromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

Synthesis 21 5-Bromo-4-methy -1-oxy-pyridin-2-ylamine hydrochloride 5-Bromo-4-methyl-pyridin-2-ylamine (22 mmol, 4.1 1 g) was dissolved in acetone (40 mL) and cooled to 0 C and then treated with m-CPBA (44 mmol, 7.59 g). The reaction mixture was allowed to stir at room temperature for 2 hours and then evaporated under reduced pressure to an orange solid. This was dissolved in chloroform cooled to 0 C and treated portion-wise with 2 M ethereal hydrogen chloride (40 mL). The cooling bath was removed and the suspension was stirred at room temperature for 3 hours. The solid precipitate was filtered off and washed with ether (1×10 mL). The solid was dried under reduced pressure to provide the title compound as beige solid. Yield: 5.27 g, 100%. LCMS, analytical method 1 , TR=2.43 mins, 100%, MI+H=203/205. H NMR (300 MHz, DMSO-d6) delta: 8.64 (1 H, s), 8.30 (2 H, m), 7.05 (1 H, s), 2.32 (3 H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98198-48-2, its application will become more common.

Reference:
Patent; CHARLES, Mark David; BROOKFIELD, Joanna Lola; EKWURU, Chukuemeka Tennyson; STOCKLEY, Martin Lee; WO2015/25172; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 136888-21-6, 2-Chloro-5-fluoro-3-nitropyridine, 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, Quality Control of 2-Chloro-5-fluoro-3-nitropyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Chloro-5-fluoro-3-nitropyridine

To 2-chloro-5-fluoro-3-nitropyridine (305 mg, 1 .728 mmol) in DMSO (5 mL) were added (1 – methyl-1 H-pyrazol-3-yl)methanamine (21 1 mg, 1 .901 mmol) and K2C03 (310 mg, 2.246 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was then quenched with water (10 mL), and the resulting precipitate was isolated by filtration, washed with water, and then dried in vacuum oven for 4 hours to afford 5-fluoro- N-((1 -methyl-1 H-pyrazol-3-yl)methyl)-3-nitropyridin-2-amine (210 mg) as a yellow color solid. LC-MS (ES) m/z = 252 [M+H]+. NMR (400 MHz, DMSO-c/6): delta 3.80 (s, 3H), 4.69 (d, J = 5.3 Hz, 2H), 6.16 (d, J = 2.3 Hz, 1 H), 7.60 (d, J = 2.3 Hz, 1 H), 8.44 (dd, J = 8.5, 2.9 Hz, 1 H), 8.66 (d, J = 2.8 Hz, 1 H), 8.69 (t, J = 5.3 Hz, 1 H).

The synthetic route of 136888-21-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 175205-81-9 ,Some common heterocyclic compound, 175205-81-9, molecular formula is C6H3BrF3N, 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: a. Palladium(0)-catalyzed reactions. A Schlenk flask was charged with Pd(dba)2 (1-8 mol %, 2.9-23 mg), phosphine ligand (1.25-9 mol %), and bromopyridine2-8 (0.5 mmol), and 5 mL of dioxane, amine 1 or 21 (0.625 mmol), and sodium tert-butoxide(0.75 mmol, 72 mg) were added. The mixture was refluxed for 12 h with stirring and cooled to room temperature, the organic phase was separated, the precipitate was washed with methylene chloride (5 mL),and the organic phase was combined with the washings and evaporated under reduced pressure. The residue was dissolved in methylene chloride (5 mL), and the solution was washed with water (3 × 5 mL), dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). b. A Schlenk flask was charged with copper(I)iodide (10 or 20 mol %, 9.5 or 19 mg), 2-isobutyrylcyclohexanone(20 or 40 mol %, 17 or 34 mg), and bromopyridine 2-8 (0.5 mmol), and 1 mL of DMF,amine 1 or 21 (0.5 mmol), and cesium carbonate(0.75 mmol, 250 mg) were added. The mixture was heated for 24 h at 140C with stirring and cooled to room temperature, the organic phase was separated,and the residue was washed with methylene chloride(5 mL). The organic phase was combined with the washings and evaporated under reduced pressure, the residue was dissolved in methylene chloride (5 mL),and the solution was washed with water (3 × 5 mL),dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). The spectral parameters of compounds 9, 16 [21], 22, and 29 [26]were consistent with published data

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,175205-81-9, its application will become more common.

Reference:
Article; Lyakhovich; Murashkina; Averin; Abel; Maloshitskaya; Savelyev; Orlinson; Beletskaya; Russian Journal of Organic Chemistry; vol. 55; 6; (2019); p. 737 – 747; Zh. Org. Khim.; vol. 55; 6; (2019); p. 829 – 840,12;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6443-85-2 ,Some common heterocyclic compound, 6443-85-2, molecular formula is C7H6N2, 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.

In a Schlenk tube,116 mg (0.151 mmol) of 1 was dissolved in 10 mL of CH2Cl2, resulting in a bright-red solution. 160 muL (179 mg, 1.51 mmol) of 3-pyridylacetonitrile (3-Py-CH2CN) was syringed into the solution, and the reaction mixture was stirred at room temperature for 7 h. After this time, the solvent was evaporated to dryness and the solid residue was washed three times with hexane. The final product was characterized as 2. Yield: 100.8 mg, 0.139 mM,92%. IR (ATR): nu 2535vs (BH), 2511vs (BH), 2460vs (BH), 2255w (CN), and 2060m(RhH). 11B-{1H} NMR (128 MHz; CD2Cl2; 298 K): delta + 12.1, +7.8, +3.5, +0.3, -3.8, -9.9,-18.5, -25.6, and -29.6. 1H NMR (500 MHz; CD2Cl2; 298 K): delta + 7.91 (1H, br,3-PyCH2CN), +7.82 (1H, br, 3-PyCH2CN), +7.35 – +7.05 (aromatics, PPh3), +4.04 (v br,BH), +3.67 (ABq, 1H, DeltanuAB = 30.8 Hz, JAB = 19.2 Hz, CH2CN), +3.55 (ABq, CH2CN),+2.85 (v br, BH), +1.84 (v br, BH), -1.37 (br s, BHB), and -12.51 (apparent q, J = 18.9 Hz, RhH); due to the insolubility of the compound, the terminal B-H peakscould not be observed. 31P-{1H} NMR (121 MHz; CD2Cl2; 213 K): delta + 36.3 (dd,JRhP = 104.1 Hz) and + 30.4 (dd, JRhP = 127.1 Hz, 2JPP = 19 Hz). LRMS (MALDI+/DCTB): m/z [2M-3(PPh3)-4H]+ obsvd 979, Calcd for P1C32H43Rh2S2B18N4: 979; [M-PPh3-2H]+ obsvd 621, Calcd for P1C25H29Rh1S1B9N2: 621. The obsvd isotope envelope matchesthat calculated from the known isotopic abundances of the constituent elements.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6443-85-2, its application will become more common.

Reference:
Article; Calvo; Kess; Macias; Sancho; Lahoz; Oro; Journal of Coordination Chemistry; vol. 67; 23-24; (2014); p. 4016 – 4027;,
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. 6937-03-7, name is Methyl 2-aminoisonicotinate, molecular formula is C7H8N2O2, 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. name: Methyl 2-aminoisonicotinate

To solution of (2,4-dichloro-phenoxyacetic acid (0.200 g, 0.9 mmol), 2-amino isonicotinic acid methyl ester (207 mg, 1.36 mmol) and DMAP (0.222 g, 1.81 mmol) in DMF 13 mL was added PyBOP (946 mg, 1.81 mmol) at room temperature. Reaction mixture was stirred at room temperature. Resulting mixture poured onto ice cold water, was diluted by ethyl acetate. The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9-4:6) to give 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.229 g, 71% yield). 1H NMR (DMSO-d6, 300 MHz) 10.87 (1H, s, CONH), 8.53 (2H, d, J=4.8 Hz, pyridine), 7.58 (m, 2H, aromatic), 7.35 (1H, dd, J=1.8&9.0 Hz, pyridine), 7.11 (1H, d, J=8.4 Hz, aromatic), 4.98 (2H, s, OCH2), 3.88 (3H, s, OCH3).

With the rapid development of chemical substances, we look forward to future research findings about 6937-03-7.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 375368-83-5, Adding some certain compound to certain chemical reactions, such as: 375368-83-5, name is 3-Bromo-6-fluoro-2-methylpyridine,molecular formula is C6H5BrFN, 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 375368-83-5.

Step A. 5-bromo-6-methylpyridin-2-ol 3-Bromo-6-fluoro-2-methylpyridine (5 g, 0.021 mol) was added into HQ (6mol/L, 40mL), and the mixture was stirred, and refluxed for 2 hours. The product was detected by TLC. After the reaction was finished, the mixture was quenched with saturated aqueous NaHC(, filtered, and concentrated to afford the title compound.

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. 375368-83-5, 3-Bromo-6-fluoro-2-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; LI, Bing; SZEWCZYK, Jason W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi P.; PIO, Barbara; DANG, Qun; LIN, Linus S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/89809; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 929617-35-6, 5-Bromo-1H-pyrazolo[3,4-c]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, COA of Formula: C6H4BrN3, blongs to pyridine-derivatives compound. COA of Formula: C6H4BrN3

General procedure: To a stirred solution of 5-bromo-1W-pyrazolo[3,4-c]pyridine (1 g, 5.07 mmol) in DMF (10mL), 60% NaH (0.405 g, 10.14 mmol) was added at 0C and it was stirred at RT for 30 min. Then, (bromomethyl)cyclobutane (1.12 g, 7.56 mmol) was added to the mixture at 0 C and it was stirred at RT for 16 h. The reaction mixture was poured into ice water (50 mL) and extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with brine (20 ml). The combined organic layers were dried over anhydrous Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The crude compound was purified by column chromatography using 10% EtOAc/pet ether as eluent to afford fraction-1 5-bromo-1-(cyclobutylmethyl)-1H-pyrazolo[3,4-c]pyridine (reference example 6) (500 mg) as an off-white solid, and 20% EtOAc/pet ether as eluent to afford fraction-2 5- bromo-2-(cyclobutylmethyl)-2W-pyrazolo[3,4-c]pyridine (reference example 7) (450 mg) as an off-white solid Reference example 6: LC-MS (method 1): Rt = 2.30 min; m/z = 265.86 (M+H+). Reference example 7: LC-MS (method 1): Rt = 2.06 min; m/z = 265.61 (M+H+).

The synthetic route of 929617-35-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
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

Adding a certain compound to certain chemical reactions, such as: 73027-79-9, 4,6-Dichloronicotinic acid, 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, SDS of cas: 73027-79-9, blongs to pyridine-derivatives compound. SDS of cas: 73027-79-9

4,6-Dichloro-N-(2-hydroxyethyl’)-N-methylpyridine-3-carboxamide,cKpgammacl oOxalyl chloride (1.12 mL, 12.50 mmol), followed by DMF (2 drops), were added to a mixture of 4,6-dichloronicotinic acid (2g, 10.42 mmol) in 4M HCl in dioxane (2.62 mL, 10.42 mmol) and DCM (40 mL). The reaction was stirred at RT for 2 hours, the volatiles removed in vacuo and the residue dissolved in DCM (20 mL). The solution was added dropwise to a mixture of 2-(methylamino)ethanol (0.93 mL, 11.46 mmol) and triethylamine (3.2 mL, 22.92 mmol) in DCM (20 mL) and the mixture stirred at RT for 20 hours. The mixture was concentrated in vacuo and ethyl acetate (100 mL) added to the residue. The organics were washed with water (100 mL), saturated sodium bicarbonate solution (50 mL), brine (50 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow oil. The residue was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound (1.8 g). 1E NuMR delta (CDCl3): 2.90 & 3.11 (2xs, 3H), 3.17 – 3.91 (m, 4H), 7.35 – 7.40 (m, IH), 8.28 – 8.33 (m, IH); m/z 249 (M+H)+; The hydroxyl-containing compounds used in the synthesis of Examples 2a-2c were prepared in an analogous fashion from 2-(methylamino)ethanol and the appropriate carboxylic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73027-79-9, 4,6-Dichloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7040; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 113118-83-5, 5-Methoxynicotinaldehyde, 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 113118-83-5, blongs to pyridine-derivatives compound. Product Details of 113118-83-5

A 250 mL round bottom flask equipped with a magnetic stirring bar, nitrogen inlet, and septum was charged with THF (100 mL) and butyllithium (7.29 mL, 18.23 mmol). After cooling to -78C, 2-(naphthalen-2-yl)acetonitrile (3.05 g, 18.23 mmol) was added, and after 60 minutes, 5-methoxynicotinaldehyde (2.5 g, 18.23 mmol) was added via syringe. After stirring at (-78C) for 3 hours, the reaction was quenched by the addition of acetic acid (2.1 mL) while stirring at -70C. The aqueous layer was extracted with Et20 (2 x 250 mL), and the combined organic extracts were washed with brine (250 mL) and dried (MgSC^). The material was concentrated in vacuo to give a crude aldol (6 g). ISCO purification on silica gel eluting with 0-100% of ethyl acetate in hexane afforded the product as an antv.syn mixture (4 g, 72%). 1H NMR (500 MHz, CDCk) delta 2.80 (d, J=3.7 Hz, 1 H), 3.78 (s, 3 H), 4.24 (d, J=5.2 Hz, 1 H), 5.12 (d, J=3.4 Hz, 1 H), 7.18 – 7.38 (m, 4 H), 7.47 – 7.61 (m, 2 H), 7.73 – 7.93 (m, 5 H), 8.04 (d, J=1.5 Hz, 1 H), 8.23 (d, J=2.7 Hz, 1 H).

The synthetic route of 113118-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH; VIRGINIA TECH INTELLECTUAL PROPERTIES, INC.; RICHELSON, Elliott; FAUQ, Abdul H.; CARLIER, Paul R.; MONCEAUX, Christopher J.; WO2014/159251; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem