Category: pyridine-derivatives

Related Products of 1563-56-0, 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. 1563-56-0, name is (2-Amino-5-bromophenyl)(pyridin-2-yl)methanone. A new synthetic method of this compound is introduced below.

38.6 g (139 mmol) of (2-amino-5-bromophenyl)-pyridin-2-yl-methanone of formula (A) and 45.2 g (153 mmol) of (2S)-2- (benzyloxycarbonylamino) -5-methoxy-5-oxo-pentanoic acid were dissolved in 200 mL of dichloromethane at a temperature of about 15C. The solution was cooled at -10C, and a previously prepared solution containing 32.2 g (156 mmol) of N,N?dicyclohexylcarbodiimide in 65 mL of dichloromethane was slowlyadded at said temperature. The reaction mixture was kept under stirring at a temperature of about -10C for 48 hours, and the salts resulting from the reaction were then filtered at a temperature of about 15C.The reaction solvent was removed by means of distillationwith a vacuum at the maximum temperature of 25C, and 250 mL ofmethyl-tert-butylether were added. The obtained mixture was heated at 50C and then slowly cooled at a temperature of about 25C. The resulting solid was filtered and oven-dried at 50C.72.3 g (93.6%) of a very slightly yellowish solid correspondingto methyl (4S)-4-(benzyloxycarbonylamino)-5-[4-bromo-2-(pyridine-2-carbonyl)aniline]-5-oxo-pentanoate of formula (I-B)were thereby obtained. The purity of the obtained products wasanalyzed by means of the ultra high performance liquidchromatography technique in Waters Acquity HClass equipment,equipped with a variable wave detector and temperature-controlled oven for the column. Figure 2 shows the 1H-NMRspectrum. 1H-NMR (CDC13, 400 MHz) (ppm) : 11.43 (1H, s) , 8.73(1H, d) , 8.56 (1H, d) , 8 (1H, d) , 7.93 (1H, s) , 7.92 (1H, s)7.67 (1H, dd) , 7.52 (1H, m) , 7.35 (SH, m) , 5.71 (1H, d) , 5.04(2H, m), 4.45 (1H, m), 3.65 (3H, s), 2.50 (2H, m), 2.31 (1H, m),2.07 (1H, m)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1563-56-0, its application will become more common.

Reference:
Patent; MOEHS IBERICA, S.L.; SANCHEZ CASALS, Carles; DOBARRO RODRIGUEZ, Alicia; (66 pag.)WO2019/72944; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1227628-78-5, 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 1227628-78-5 as follows.

To a solution of (R)-5-(2-hydroxy-l-phenylethyl)-amino)-pyridin-3-yl)-boronic acid (100 mg, 0.5 mmol) in DME/H20 (5 : 1, 6 mL) was added Pd(PPh3)4 (1 16 mg, 0.1 mmol), K2C03 (138 mg, 1.0 mmol) and 5-bromo-lH-pyrazolo[4,3-b]pyridine (125 mg, 0.5 mmol). The resulting mixture was degassed and then stirred for 10 hours at 95 C under an Ar atmosphere. After cooling, the mixture was diluted with water (30 mL) and then extracted with EtOAc (2 x 50 mL). The combined organic layers were washed with water and brine, and then dried. The solvent was concentrated and the residue was purified by Prep-HPLC to give (R)-2-phenyl-2-[5-(lH- pyrazolo[4,3-b]pyridin-5-yl)-pyridin-3-ylamino]-ethanol (5 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227628-78-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; YANG, Song; ZHOU, Chengang; WO2014/90692; (2014); 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.55240-51-2, name is 2-Phenylisonicotinic acid, molecular formula is C12H9NO2, molecular weight is 199.21, as common compound, the synthetic route is as follows.name: 2-Phenylisonicotinic acid

To a flask containing 1 10 mg (0.553 mmol) of Hppy-C02H, 275 mg (0.529 mmol) of Ru(bpy)2Cl2, 183 mg (1.08 mmol) of AgN03, and 28 mg (0.70 mmol) of NaOH was added 30 mL of a degassed aqueous methanol solution (H20:MeOH 1 :5 v/v). The reaction mixture was heated at reflux for 18 hrs, cooled, and then filtered through celite to afford a dark red/orange filtrate. The solvent was removed in vacuo and then passed through a silica column (acetone:MeOH:KN03 (sal, aq) 2: 1 : 1). The sample was passed through a silica column (MeOH:CHCl3 3: 1) a second time and 56 mg of a red-purple product was obtained after recrystallization from CH2CI2 and hexanes (yield = 14 %). NMR (CD3OD): 6.42 (dd, 1H, J = 7 Hz, l = 1 Hz), 6.79 (td, 1H, J = 7 Hz, l = 1 Hz), 6.89 (td, 1H, = 7 Hz, 4./ = 1 Hz), 7.19-7.28 (m, 3H), 7.31 , (dd, 1H, J = 6 Hz, 4 J = 2 Hz), 7.46 (ddd, 1H, 3 J = 7 Hz, 5 Hz, 4 J = 1 Hz), 7.58 (d, 1H, 3 J = 6 Hz, 4 J = 1 Hz), 7.72- 7.91 (m, 7H), 8.02 (ddd, 1H, 3 J = 8 Hz, 8 Hz, J = 1 Hz), 8.10 (ddd, 1H, J = 5 Hz, 4J = 2 Hz, = 1 Hz), 8.41 (d, 1H, J = 8 Hz), 8.45 (d, 1H, 4 J = 1 Hz), 8.45 (d, 1H, J = 8 Hz), 8.51 (d, 1H, J = 8 Hz), 8.61 (d, 1H, J = 8 Hz). ESI-MS: m/z, 612.0 (calcd for {M+} 612.1) 13C NMR (CD3OD with 1 drop of NaOD): 194, 172, 169, 159, 159, 158, 157, 156, 151 , 151 , 151 , 150, 147, 146, 138, 136, 136, 135, 135, 130, 128, 128, 127, 127, 125, 125, 125, 124, 124, 123, 122, 1 19. Anal. Calcd. for C32H24N605Ru + CH3OH: C, 56.17; H, 4.00; N, 1 1.91. Found: C, 57.45; H, 4.40; N, 10.38.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55240-51-2, 2-Phenylisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; BERLINGUETTE, Curtis P.; KOIVISTO, Bryan; ROBSON, Kiyoshi; WO2011/32269; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 123531-52-2, Adding some certain compound to certain chemical reactions, such as: 123531-52-2, name is Ethyl imidazo[1,2-a]pyridine-3-carboxylate,molecular formula is C10H10N2O2, 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 123531-52-2.

Ethyl imidazo[1,2-a]pyridine-3-carboxylate(0.90 g, 4.7 mmol) and hydrazine (1.0 mL, 13 mmol, 40%) are combined in EtOH (10 mL). The mixture is stirred under microwave conditions at 100 C. for 2 hrs. The solvent is removed to give the title compound (0.82 g, 93%) which can be used without further purification. LC/MS (m/z): 177 (M+H).

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. 123531-52-2, Ethyl imidazo[1,2-a]pyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; Hu, Zhi Long; Liu, Lian Zhu; Ma, Tianwei; Zhang, Haizhen; Zhou, Jingye; (25 pag.)US2018/194755; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 109-09-1, 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. 109-09-1, name is 2-Chloropyridine, molecular formula is C5H4ClN, 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.

Asolution of 2-chloropyridine ( XI) (9.39 mL, 0.1 mol) in, anhydrous THF (50 mL) was added slowly to a solution of LDA (2.0 M solution in THF/ hexane/ethylbenzene, 50 mL, 0.1 mol) in THF (200 mL) stirred at -78 C. under nitrogen. The stirring was continued at -78 C. for an additional 3 h before adding acetaldehyde (6.17 mL, 0.110 mol). The solution was stirred at -78 C. for another 2 h before allowing the temperature to rise to -40 C. A solution of water (4 mL) in THF (40 mL) was added slowly to the solution. When the temperature reached -10 C., additional water (200 mL) was added to the solution. The solution was extracted with ethyl ether (3×100 mL). The combined organic phase was dried over MgSO4, filtered and evaporated under reduced pressure to get a brown viscous residue. The crude product was purified on a flash silica gel column (1:1 DCM:hexane?100% DCM) to produce 1-(2-chloropyridin-3-yl)ethanol (XII) as a brown viscous oil (6 g, 38.1 mmol, 38% yield). 1H NMR (CDCl3) delta ppm 1.52 (d, J=6.41 Hz, 3H), 2.51 (brs, 1H), 5.24 (m, 1H), 7.28 (m, 1H), 7.97 (dd, J=7.72 Hz, J=1.70 Hz, 1H), 8.27 (dd, J=7.72 Hz, J=1.79 Hz, 1H).

According to the analysis of related databases, 109-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark; US2013/296302; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7205-46-1 ,Some common heterocyclic compound, 7205-46-1, molecular formula is C7H6ClN3, 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.

4-Amino-3-ethyl-phenol (100 mg, 0.73 mmol, 1.0 equiv), 6-Chloro-l -methyl- 1H- imidazo[4,5-c]-pyridine (134 mg, 0.80 mmol, 1.1 equiv), Cs2C03 (714 mg, 2.19 mmol, 3.0 equiv), BetaGammaNuAlphaRho (46 mg, 0.07 mmol, 0.1 equiv), and Pd2(dba)3 (33 mg, 0.04 mmol, 0.05 equiv) were dissolved in dry dioxane (5 mL) under N2 atmosphere. The mixture was sonicated for 5 mn under N2 flow and then re fluxed for 20h. Full conversion was observed by LCMS. It was then cooled down and concentrated to dryness, diluted in DCM and washed with water (3x 20 mL). The aqueous layer was extracted with DCM (3x 30 mL) and the combined organic layer was dried over Na2SO i, filtered and concentrated to dryness. Purification was performed by column chromatography using the following eluant: EtOAc/Petroleum Ether (1 : 1) to EtOAc (over 5 CV), MeOH/EtOAc (1 : 19) (10 CV), MeOH/EtOAc (1 :9) (10 CV) to afford the desired compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7205-46-1, its application will become more common.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; SCHMITT, Benoit Antoine; GENEY, Raphael Jean Joel; DOYLE, Kevin James; PEACH, Joanne; PALMER, Nicholas John; JONES, Graham Peter; HARDY, David; DUFFY, James Edward Stewart; WO2013/117645; (2013); 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. 800402-12-4, name is 2-Chloro-5-iodo-4-pyridinamine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-5-iodo-4-pyridinamine

2-(3-(4-Amino-6-chloropyridin-3-yl)prop-2-ynyl)-6-(thiophen-2- yl)pyridazin-3(2H)-one. A mixture o f Et3N (200 mul, 1435 mumol), Cu(I) (10 mg, 53 mumol), PdCl2(PhP3)2 (20 mg, 28 mumol), 2-(prop-2-ynyl)-6-(thiophen-2- yl)pyridazin-3(2H)-one (90 mg, 416 mumol), and 2-chloro-5-iodopyridin-4-amine (138 mg, 542 mumol) in MeCN (1.5 mL) was heated to 80 0C under nitrogen for 1 h. The mixture was cooled to room temperature, and was loaded to a silica column. Chromatography with 0.5-5% MeOH in CH2Cl2 afforded a pink solid which was triturated with EtOAc-hexane (1 :2, 10 mL) to give a pink solid as the pure product (48 mg). MS (ESI pos. ion) calc’d for Cj6Hi 1CIN4OS: 342.0; found 343.1 (MH+). 1H NMR (400 MHz, Chloroform-d) delta ppm 5.18 (s, 2 H) 5.75 (br. s., 2 H) 6.64 (s, 1 H) 7.03 (d, J=9.78 Hz, 1 H) 7.11 (dd, J=5.09, 3.72 Hz, 1 H) 7.37 – 7.48 (m, 2 H) 7.73 (d, J=9.78 Hz, 1 H) 8.03 (s, 1 H).

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, 800402-12-4, 2-Chloro-5-iodo-4-pyridinamine.

Reference:
Patent; AMGEN INC.; WO2008/103277; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76041-71-9, 3-Chloro-2-hydroxy-5-(trifluoromethyl)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, Recommanded Product: 76041-71-9, blongs to pyridine-derivatives compound. Recommanded Product: 76041-71-9

Preparation of N-({[3-chloro-5-(trifluoromethyl)pyridin-2-ylloxy}methyl)-2- (trifluoromethyl)benzamide (compound 1)To a solution of 0.20Og (1.01 mmol) of 3-chloro-5-(trifluoromethyl)pyridin- 2-ol in 5 ml of a mixture tetrahydofurane/NaOH IM (4/1) was added 0.263g {[2- (trifluoromethyl)benzoyl]amino}methyl acetate (1.01 mmol). The mixture was stirred 14 hours at room temperature.The reaction mixture was poured into 10ml of diethyl ether. Afire separation of the phases, the organic phase was washed twice with 5ml of water and dried over magnesium sulphate.After filtration, the solvent was evaporated and the residue was purified by flash chromatography on silica gel (eluent: heptane/ethyl acetate: 6/4) to give N-({[3- chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}methyl)-2-(trifluoromethyl)benzamide: 298 mg (74%). Mass spectrum : 399 (M+ 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76041-71-9, 3-Chloro-2-hydroxy-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE SA; WO2008/3744; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 101083-92-5 ,Some common heterocyclic compound, 101083-92-5, molecular formula is C7H5N3O2, 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.

EXAMPLE 43; [0221] This example illustrates a preparation of 6-methoxy-2-(l-methyl-lH-pyrrolo[2,3- delta]pyridin-5-yl)isoindolin-l-one in an embodiment of the invention.; Step A: Synthesis of l-methyl-5-nitro-7-azaindole,; [0222] A solution of 5-nitro-7-azaindole (0.195 g, 1.2 mmol) in DMF (10 mL) was treated with NaH (60%, 0.057 g, 1.44 mmol), followed by iodomethane (0.204 g, 1.44 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then poured into water (200 mL) and extracted with dichloromethane (3 chi100 mL). The combined organic layer was washed with brine (100 mL), dried over sodium sulfate, and concentrated. The crude product was purified by chromatography (silica, 50:50 ethyl acetate/hexanes) to yield l-methyl-5-nitro-7-azaindole (0.152 g, 72%) as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 9.23 (d, J= 2.4 Hz, IH), 8.76 (d, J= 2.4 Hz, IH), 7.36 (d, J= 3.6 Hz, IH), 6.66 (d, J= 3.5 Hz, IH), 3.96 (s, 3H).

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. 101083-92-5, 5-Nitro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The United States of America, as represented by the Secretary, Department of Health and Human Services; Science Applications International Corporation (SAIC); Albany Molecular Research, Inc.; WO2009/42907; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 78607-36-0, 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. 78607-36-0, name is 2-Chloro-3-iodopyridine. A new synthetic method of this compound is introduced below.

To a flame-dried flask were added Pd(PPh3)4 (10 mol %), Xantphos (10 mol %), Cs2CO3 (3 eq) and 2-chloro-3-iodopyridine (1.2 eq). Then, 1SI (1 eq) and DMF (0.15 M) were added to the reaction mixture under an N2 atmosphere. The reaction mixture was stirred for 10 min at room temperature, and then heated at 140 C. in a pre-heated oil bath for 24 h. After that, the reaction mixture was cooled to room temperature, diluted with CH2Cl2, filtered through a short pad of Celite, and washed with CH2Cl2. The combined organic extracts were concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel to provide the product DFE-1S-2 in 67% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,78607-36-0, 2-Chloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Arizona Board of Regents on behalf of Arizona State University; Li, Jian; Zhu, Zhi-Qiang; (232 pag.)US2018/337345; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem