Tag: M.W:100-200

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 62150-45-2, name is 4-Bromopyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Bromopyridine-2-carbonitrile

Step 1. 4-[1-(4-Chlorobenzyl)-1H-pyrazol-4-yl]pyridine-2-carbonitrile 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.60 g, 3.1 mmol, Aldrich) in DMF (16 mL) was treated with 1-(bromomethyl)-4-chlorobenzene (0.70 g, 3.4 mmol, Aldrich) and K2CO3 (1.3 g, 9.3 mmol). After stirring for 2 hours, the mixture was partitioned between water and EtOAc. The organic layer was washed with water, followed by brine, dried over Na2SO4, filtered, and concentrated. The crude product (0.90 g, 2.8 mmol) was combined with 4-bromopyridine-2-carbonitrile (0.45 g, 2.4 mmol, Synthonix), CsF (1 g, 6 mmol), and 4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium (2:1) (0.15 g, 0.22 mmol, Aldrich) in 1,4-dioxane (6 mL, 70 mmol) and water (1 mL, 70 mmol). The mixture was degassed and heated to 100¡ã C. for 10 minutes. Upon cooling to room temperature, the mixture was partitioned between water and EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-70percent EtOAc in hexanes. Yield: 0.38 g, 44percent.

With the rapid development of chemical substances, we look forward to future research findings about 62150-45-2.

Reference:
Patent; Incyte Corporation; Sparks, Richard B.; Shepard, Stacey; Combs, Andrew P.; Buesking, Andrew W.; Shao, Lixin; Wang, Haisheng; Falahatpisheh, Nikoo; (158 pag.)US2017/190689; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67346-74-1, 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. 67346-74-1, name is 3-Ethynylpyridin-2-amine. A new synthetic method of this compound is introduced below.

Reference Example 48 3-(3-(5-p-Tolyloxy-thiophen-2-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamine; To a tetrahydrofuran (7.00 mL) solution of (5-p-tolyloxy-thiophen-2-yl)-acetohydroximoyl chloride (191 mg, 0.678 mmol) described in Manufacturing Example 48-1-5 and 3-ethynyl-pyridin-2-ylamine (40.0 mg, 0.339 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (189 muL, 1.36 mmol) at room temperature, which was stirred for 4 hours at room temperature. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate_heptane=1:3) to obtain the title compound (2.03 mg, 1.65percent).1H-NMR Spectrum (DMSO-d6) delta (ppm): 2.32 (3H, s), 4.14 (2H, s), 5.54 (2H, brs), 6.34-6.36 (1H, m), 6.40 (1H, s), 6.62-6.63 (1H, m), 6.73-6.77 (1H, m), 6.98-7.00 (2H, m), 7.11-7.13 (2H, m), 7.76-7.78 (1H, m), 8.14-8.15 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67346-74-1, 3-Ethynylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3167-49-5, 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. 3167-49-5, name is 6-Aminonicotinic acid. A new synthetic method of this compound is introduced below.

[1148] A mixture of bromoacetaldehyde diethylacetal (8.0 ml, 52.5 mmol), H2O (60 ml), and conc. HCl (2.6 ml) is heated to 90 C. with an oil bath for 2 h. 6-aminonicotinic acid (2.5 g, 18.1 mmol) and sodium bicarbonate (4.3 g, 50.7 mmol) are added to the solution at rt, followed by heating the resulting mixture to 60 C. with an oil bath for 30 min. Upon cooling to rt a white ppt. is formed. The resulting off white solid is recrystallized from H2O/EtOH/Et2O to afford white crystals (2.3 g, 10.6 mmol, 59%) for imidazo[1,2-a]pyridine-6-carboxylic acid. HRMS (FAB) calcd for C8H6N2O2+H 163.0508, found 163.0492.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3167-49-5, 6-Aminonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Rogers, Bruce N.; Piotrowski, David W.; Walker, Daniel Patrick; Jacobsen, Eric Jon; Acker, Brad A.; Wishka, Donn G.; Groppi JR., Vincent E.; US2003/236264; (2003); 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.53277-47-7, name is Methyl 2-chloro-6-methylnicotinate, molecular formula is C8H8ClNO2, molecular weight is 185.61, as common compound, the synthetic route is as follows.Quality Control of Methyl 2-chloro-6-methylnicotinate

Methyl 6-bromomethyl-2-chloronicotinate Methyl 2-chloro-6-methyinicofinate from Example F1 (5.70 g, 30.8 mmol) was reacted following the method of Example of A1. The product was purified by flash chromatography on silica (eluant EtOAC:pet. ether 20:80); yield 4.8 g (58%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53277-47-7, Methyl 2-chloro-6-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Ashworth, Doreen; Pitt, Gary R W; Hudson, Peter; Yea, Christopher; Franklin, Richard J; Semple, Graeme; Jenkins, David Paul; US2004/38962; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13534-99-1, 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. 13534-99-1, name is 2-Amino-3-bromopyridine. A new synthetic method of this compound is introduced below.

The compound 14-1 (200 mg) was dissolved in a mixed solvent of tetrahydrofuran (1.2 ml) and triethylamine (7 ml). Ethynyl (trimethyl) silane (227 mg) , copper (I) iodide (8.8 mg) and dichloropalladium- triphenyl phosphine (32.5 mg) were added and the mixture was sealed in a tube. After stirring the mixture at 900C for 22 hours, the reaction mixture was added to water to terminate the reaction. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain the title compound (244 mg) . IH NMR (400 MHz, CDCl3) (ppm) : 0.26 (s, 9H), 5.08 (br. s., 2H), 6.62 (br. s., IH), 7.54d, J=7.2 Hz, IH), 8.05 (br. s. , IH) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-99-1, 2-Amino-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management CO., LTD.; MOTOKI, Takafumi; KANEKO, Toshihiko; YAMAMOTO, Noboru; KHAN, Afzal; WO2010/13794; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 68325-15-5, 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 68325-15-5, name is 3-Chloro-4-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 1.39 g of 3-chloro-isonicotinonitrile, 1.10 g of 2,2,2- trifluoroethanol and 5 mL of DMF, 0.40 g of 60% sodium hydride (oily) was added under ice cooling, followed by stirring for 20 minutes, heating to room temperature and further stirring for 7.5 hours. After ice cooling again, 0.20 g of 60% sodium hydride (oily) was added, followed by heating to room temperature and further stirring for 15 hours. Under ice cooling, water was added and the precipitated crystal was washed with water, collected by filtration and then dried under reduced pressure to obtain 1.63 g of 3-(2,2,2-trifiuoroethoxy)- isonicotinonitrile.1 H-NMR (CDC13 ) delta : 8.53-8.52(br m, IH), 8.5 l(d, J=4.9Hz, IH), 7.53(dd, J=4.9, 0.6Hz, IH), 4.62(q, J=7.7Hz, 2H)

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 68325-15-5, 3-Chloro-4-cyanopyridine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49220; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14254-57-0, 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. 14254-57-0, name is Isonicotinoyl chloride, molecular formula is C6H4ClNO, 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.

Example 1Synthesis of(3-chloro-4-methoxyphenyJ)-(2-pyridin-4-ylquinolin-4-yl) amine (E 1) Step (i): Synthesis ofN-(2~acetylphenyl) isonicotinamide (1); To a mixture of orthoaminoacetophenone (2.0 grams, 14.8 mmol) and triethylamine (7.2 mL, 52.0 mmol) in dry tetrahydrofuran (15 niL) was added EPO dropwise to a freshly prepared isonicotinyl chloride (2.5 grams, 17.8 mmol) dissolved in 50 mL of tetrahydrofuran, while the mixture was stirred under a nitrogen atmosphere at 0 0C. After this mixture was stirred at 0 0C for 2 hours, the reaction mixture was allowed to warm to room temperature, and stirred overnight. The resulting mixture was poured into ice-cold water and partitioned in ethyl acetate (2 x 250 mL). The organic layers were collected and washed with water (100 mL) followed by saturated sodium chloride (125 mL) solution, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue thus obtained was purified by column chromatography using ethyl acetate and petroleum ether, followed by washing with diethyl ether to afford the desired product (1) as a pink colored solid (0.975 gram); Yield: 28%.1H NMR (CDCl3, 200 MHz):delta 12.89 (br s, D2O exchangeable, NH), 8.94 (d, J = 8.4 Hz, IH), 8.83 (d, J = 5.6 Hz, 2H), 7.99 (d, J = 7.8 Hz, IH), 7.90 (d, J = 5.9 Hz, 2H), 7.65 (t, J – 8.1 Hz, IH), 7.20 (d, J = 7.6 Hz, IH), 2.74 (s, 3H). IR (KBr, cm”1): 3439.7, 1675.0, 1644.4, 1522.5, 1249.0, 757.5. MS: (CI) m/z: 241 (M++l).

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 14254-57-0, Isonicotinoyl chloride.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; PAL, Manojit; KHANNA, Ish; SUBRAMANIAN, Venkataraman; PADAKANTI, Srinivas; PILLARISETTI, Sivaram; WO2006/58201; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 882033-66-1, 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. 882033-66-1, name is 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4ClFN2, 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.

Example 222A mixture of 4-chloro-5-fluoro-lH-pyrrolo [2, 3-b] pyridine (30 mg) and cyclohexylamine (87 mg) in DMI(O.4 mL) was heated in the microwave reactor (2000C, 4 hours) . The reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc (10 mL) and half-saturated aqueous sodiumhydrogencarbonate (1OmL) . The aqueous phase was extracted with EtOAc (2x 10 mL) and combined organic layers were washed with brine (20 mL) , dried over MgSO4, and concentrated. Purification of the crude product by preparative silica gel thin-layer chromatography (EtOAc) gave N-cyclohexyl-5-fluoro- lH-pyrrolo [2, 3-b]pyridin-4-amine (5 mg) as a yellow solid. 1H-NMR (CDCl3) delta: 9.90 (IH,br) , 7.95 (IH, d, J=4.4Hz) , 7.14 (IH, d, J=3.4Hz) ,6.50(lH,d,J=3.4Hz),4.46(lH,br) , 3.90-3.80 (IH,m) ,2.2-1.2 (1OH,m) . MS(ESI) :m/z 234(M+H)+.

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 882033-66-1, 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5654-95-5, 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 5654-95-5, name is 1H-Pyrrolo[2,3-b]pyridine-2,3-dione. This compound has unique chemical properties. The synthetic route is as follows.

Method 1: Under argon atmosphere at 90 C, a solution of thallium(III) acetate (1.91 g, 5 mmol) in glacial acetic acid (25 mL) was added dropwise within 2 h to a solution of 1 (1.075 g, 9.1 mmol) in glacial acetic acid (7.5 mL). The mixture was stirred overnight at 90 C, cooled with ice and the solvent was removed by evaporation. The residue was extracted with ethyl acetate, filtered and the product was purified by repeated crystallization from ethyl acetate (red violet crystals, yield: 130 mg, 10.9%).Method 2: Acid condensation. 7-Azaisatin (67.1 mg, 0.45 mmol) and 7-azaindoxyl-3-acetate (70 mg, 0.4 mmol) were suspended under argon atmosphere in acetic acid (4 mL) and conc. HCl (340 muL). The mixture was stirred at room temperature for overnight and diluted with water (30 ml). The precipitate was filtrated and purified by recrystallization from 1 N HCl/EtOH (75 mg, 0.28 mmol, 62.2%).1H NMR (400 MHz, DMSO-d6, delta = 2.49 ppm): 11.58 (s, 1H), 10,74 (s, 1H), 8.84 (dd, 1H, 3JH,H = 7.9 Hz, 4JH,H = 1.7 Hz), 8.50 (dd, 1H, 3JH,H = 4.8 Hz, 4JH,H = 1.7 Hz), 8.15-8.11 (m, 2H), 7.15-7.07 (m, 2H). 13C-{1H} NMR (150 MHz, DMSO-d6, delta = 39.5 ppm): 186.3, 170.5, 163.4, 155.8, 155.4, 147.8, 138.7, 133.8, 131.5, 118.2, 117.9, 115.5, 112.9, 105.7. C14H8N4O2¡¤0.67 H2O. Found: C 60.89, H 3.35, N 19.85; requires: C 60.87, H 3.41, N 20.28.

According to the analysis of related databases, 5654-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cheng, Xinlai; Merz, Karl-Heinz; Vatter, Sandra; Christ, Jochen; Woelfl, Stefan; Eisenbrand, Gerhard; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 247 – 255;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86604-79-7 ,Some common heterocyclic compound, 86604-79-7, molecular formula is C8H10N2O3, 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.

Step 4; [00286] Jifj-2,3,5-Dimethyl-4-nitropyridine-l -oxide: A dry heavy-walled teflon screw cap glass tube equipped with a magnetic stirrer was charged with 2,3,5-trimethyl-4- nitropyridine-1 -oxide (5 g, 27.5 mmol), potassium carbonate (3.8 g, 27.5 mmol) and deuterium oxide (30 mL) under nitrogen. The apparatus was sealed and the mixture was placed in an oil bath at about 15O0C for about 2 hours. The reaction was cooled to ambient temperature, and sodium chloride (1Og) and brine (50 mL) were added. The title product, 4.2 g of a yellow solid with identical TLC behavior as the starting material (Rf = 0.3 in 10% methanol-DCM), was isolated using standard extractive work up. The above process was repeated to afford 3.25 g of product that had deuterium incorporation of 98.1% as determined by GC-MS analysis. Yield: 65%. GC-MS: [M]+: 192 (81.6%, 2,3,5-trimethyl-4- nitropyridine-1 -oxide-dio), 191 (18.3%, 2,3,5-trimethyl-4-nitropyridine-l-oxide-d9). Step 4[00294] fi(m-2,3,5-Dimethyl-4-nitropyridine-1 -oxide: The title compound was made by following the procedure set forth in Example 1, step 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,86604-79-7, its application will become more common.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; WO2008/127640; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem