Pyridine-derivatives

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

Reference of 89284-61-7 , The common heterocyclic compound, 89284-61-7, name is 4-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

Intermediate 35 (0.10 g, 0.383 mmol) was dissolved in anhydrous THF (3.99 mL), and 60% wt. in mineral oil) (0.034 g, 0.842 mmol) was added in one portion at 0 C. After 30 4-chloronicotinonitrile (0.133 g, 0.957 mmol) and was added in one portion, and the on mixture was allowed to reach rt overnight (16 h). Afterwards, the reaction mixture was hed with NH4Cl (2 mL), diluted with EtOAc (50 mL), washed with water (2×10 mL), (1×20 mL), dried (Na2SO4), filtered, concentrated, and purified by normal phasematography to give Example 44A (138 mg, 99%). MS (ESI) m/z: 364.1 (M+H)+. Example 44B. Preparation of 4-((aR)-6-aminospiro[3.3]heptan-2- y)nicotinamide NH2

The synthetic route of 89284-61-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; LADZIATA, Vladimir; DELUCCA, Indawati; PINTO, Donald, J., P.; ORWAT, Michael J.; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; YANG, Wu; SHAW, Scott A.; GLUNZ, Peter W.; PANDA, Manoranjan; (612 pag.)WO2017/123860; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 866755-20-6, 2,6-Dichloro-3-bromopyridine, 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: 866755-20-6, blongs to pyridine-derivatives compound. SDS of cas: 866755-20-6

Fresh cut sodium (0.101 g 4.41 mmol) was added to EtOH (50 mL) . The resulting mixture was stirred at rt. After the solid dissolved 3-bromo-2 6-dichloropyridine (1 g 4.41 mmol) was added. The resulting mixture was stirred at 70 overnight. After LCMS analysis showed the starting material was disappeared. The solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with H2O (20 mL) and brine (20 mL) . The organic layer was dried over Na2SO4 filtered and concentrated. The residue was purified by silica column chromatography (PE/EA 20/1) to yield a white solid of a mixture of 3-bromo-2-chloro-6-ethoxypyridine 3-bromo-2 6-diethoxypyridine and 3-bromo-6-chloro-2-ethoxypyridine (930 mg 3.85 mmol 87yield) 1HNMR(400 MHz CD3OD) delta 7.85 (d J 1.2 Hz 1H) 6.88 (d J 8.0 Hz 1H) 4.42-4.36 (m 2H) 1.39 (t J 7.2 Hz 3H) ES-LCMS m/z 235.9 237.9 (M+H)

The synthetic route of 866755-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6188-23-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 6188-23-4 as follows.

To a solution of 6-bromoimidazo[1,2-a]pyridine (318 mg, 1.61 mmol) in 1,4-dioxane (15 mL) were added N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonamide (600 mg, 1.69 mmol), KOAc (316 mg, 3.22 mmol), H2O (3 mL) and Pd(dppf)Cl2.CH2Cl2 (131 mg, 0.161 mmol). The reaction was heated to 85 C. and stirred further for 5 hours under N2 atmosphere, then cooled to rt, and concentrated in vacuo. The residue was dissolved in DCM (200 mL) and the resulted mixture was filtered through a CELITE. The filtrate was washed with H2O (100 mL) and brine (100 mL). The combined aqueous layers were extracted with DCM (50 mL*3). The combined organic extracts were dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a flash silica gel column chromatography (DCM/MeOH (v/v)=65/1) to give the title compound as a yellowish solid (342 mg, 62%). MS (ESI, pos. ion) m/z: 345.0 [M+H]+; 1H NMR (600 MHz, DMSO-d6): delta 9.42 (s, 1H), 8.91 (s, 1H), 8.35 (d, J=2.1 Hz, 1H), 7.99 (s, 1H), 7.93 (d, J=2.4 Hz, 1H), 7.68-7.61 (m, 2H), 7.54 (dd, J=1.8, 9.6 Hz, 1H), 3.98 (s, 3H), 2.82-2.74 (m, 1H), 1.00-0.89 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6188-23-4, its application will become more common.

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