Category: pyridine-derivatives

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. 504-24-5, name is 4-Aminopyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H6N2

Example 25A 2,2-dimethyl-N-pyridin-4-ylpropanamide A mixture of 4-aminopyridine (10 g, 106 mmol) and pivaloyl chloride (12.9 g, 107 mmol) in 200 mL dichloromethane was cooled to 0 C. and treated slowly with triethylamine (10.9 g, 108 mmol), warmed to room temperature, stirred overnight, and diluted with water. The aqueous layer was extracted three times with dichloromethane and the combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The product was recrystallized from toluene to provide the desired product (14 g, 74%).

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Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
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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. 62150-45-2, name is 4-Bromopyridine-2-carbonitrile. A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Bromopyridine-2-carbonitrile

Step 1. 5-Chloro-3,4′-bipyridine-2-carbonitrile A degassed mixture of 4-bromopyridine-2-carbonitrile (0.99 g, 5.4 mmol, Synthonix), (5-chloropyridin-3-yl)boronic acid (0.847 g, 5.38 mmol, Aldrich), CsF (2.4 g, 16 mmol), and 4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium (2:1) (0.38 g, 0.54 mmol, Aldrich) in 1,4-dioxane (10 mL) and water (3 mL) was heated to 90-105° C. for 2.5 hours. The reaction mixture was filtered and the volume was reduced via rotary evaporation. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed sequentially with water and brine, dried over sodium sulfate, filtered, and concentrated. The resulting solid was triturated with MTBE (5 mL). The solid product was isolated by filtration and air dried. Yield: 0.95 g, 82percent. LCMS (M+H)+: 216.0/218.0.

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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;,
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Adding a certain compound to certain chemical reactions, such as: 6959-47-3, 2-(Chloromethyl)pyridine hydrochloride, 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: 2-(Chloromethyl)pyridine hydrochloride, blongs to pyridine-derivatives compound. Recommanded Product: 2-(Chloromethyl)pyridine hydrochloride

The ligand L1 was synthesized via previously reported procedure[23]. A solution of potassium carbonate (2.55 g, 18.45 mmol)in 10 mL water was dropwise added to the aqueous solution of 2-(chloromethyl)-pyridine hydrochloride (1.5 g, 9.15 mmol in10 mL). After about 30 min. of stirring at room temperature, thereaction mixture was extracted with dichloromethane(3 20 mL). The combined organic extracts were dried over anhydroussodium sulfate. The solution was filtered and the solvent wasremoved under vacuum. The resulted residue was then dissolvedin dichloromethane (10 mL). The dichloromethane solution of 2-chloromethyl-pyridine was added dropwise to a solution of N,N0-dimethylethylenediamine (0.471 mL, 5.34 mmol) in dichloromethane(15 mL). After this addition, 10 mL of aqueous sodiumhydroxide (1 M) was added slowly and the reaction mixture wasstirred for next 60 h at room temperature. After stirring was finished,another fraction of sodium hydroxide (10 mL, 1 M) wasadded rapidly. The reaction mixture was extracted with dichloromethane(3 25 mL) and combined organic portion was dried overanhydrous sodium sulfate. Evaporation of solvent led to isolationof the ligand L1 as a dark orange oil. (1.13 g, Yield 79%) 1H NMR(500 MHz, Methanol-d4) d 7.27 (m, 2H, pyridine ring), 7.50 (d,2H, pyridine ring), 7.76 (m, 2H, pyridine ring), 8.45 (d, 2H, pyridinering), 3.68 (s, 4H, -N-CH2-Py), 2.63 (s, 4H, -CH2-CH2-), 2.26 (s, 6H,N-CH3). IR (cm1): 2945, 2789, 1589, 1569, 1472, 1432, 1360,1304, 1146, 1090, 1031, 994, 635, 614, 418.

The synthetic route of 6959-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Nirupama; Niklas, Jens; Poluektov, Oleg; Van Heuvelen, Katherine M.; Mukherjee, Anusree; Inorganica Chimica Acta; vol. 455; (2017); p. 221 – 230;,
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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. 85838-94-4, name is tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate, molecular formula is C10H17NO2, 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. HPLC of Formula: C10H17NO2

To a solution of tert-butyl5,6-dihydropyridine-1(2H)-carboxylate (0.3627 g, 1.979 mmol) in CH2Ch (5 ml) at ooc was5 added a solution of mCPBA (0.53 g, 3.07 mmol) in CH2Cb (5 ml). The resulting reactionmixture was allowed to warm to rt and stirred over the weekend. The reaction was partitionedbetween EtOAc and 5% Na2S20 3. After separation of layers, the organic layer was washed withsat. NaHC03. brine, dried over anhydrous MgS0 4, filtered and concentrated to give the titlecompound as colorless oil.

With the rapid development of chemical substances, we look forward to future research findings about 85838-94-4.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHOBANIAN, Harry; PIO, Barbara; GUO, Yan; DING, Fa-Xiang; DONG, Shuzhi; WALSH, Shawn, P.; JIANG, Jinlong; KIM, Dooseop; WO2015/95097; (2015); A2;,
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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. 19755-53-4, name is 2-Bromo-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Bromo-3-nitropyridine

Example 16; 1-(2-(benzo[b]thiophen-2-yl)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea; 16a. 2-(benzo[b]thiophen-2-yl)-3-nitropyridine; To a solution of 2-bromo-3-nitropyridine (75 mg, 0.371 mmol) in DME (3 mL) was added benzofuran boronic acid (132 mg, 0.802 mmol), followed by Pd(PPh3)4 (35 mg, 0.03 mmol) and K2CO3 (145 mg, 1.05 mmol). The reaction mixture was stirred at 80 C. for 16 h. The mixture was filtered and washed with CH2Cl2 (10 mL). The solvent was evaporated under reduced pressure and purified by column chromatography using 0 to 80% EtOAc in hexane over 40 min as eluting gradient to afford 16a (38 mg, 40%) as a yellowish powder. MS (ES) m/z 257 [M+H]+.

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Reference:
Patent; Bristol-Myers Squibb Company; US2006/293336; (2006); A1;,
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Pyridine | C5H5N – PubChem

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. 5345-47-1, name is 2-Aminonicotinic acid. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Example 7 Synthesis of Compound 33 General Method for the SYNTHESIS of Compounds 26-44 [0096] This example illustrates Reaction Scheme IV. Preparation OF IVA : [0097] 2-Amino NICOTINIC acid (SOG, 0. 362 mole) was dissolved in 500ml methanol and treated with thionyl chloride (66MOL, 107. 6g, 0. 905MOLLE) dropwise over 30 min. Reaction mixture was heated to reflux for 3 days. Removed solvent under vacuum, residue taken up in chloroform, washed with 5% HCl (50ml), 10% sodium bicarbonate (50ml), water, and chloroform layer dried over sodium sulfate (ANH). Removed solvent to give 27G product (49. 1 % yield).

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Reference:
Patent; SCIOS INC.; WO2005/32481; (2005); A2;,
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Pyridine | C5H5N – PubChem

Application of 19798-80-2, 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. 19798-80-2, name is 4-Chloropyridin-2-amine, molecular formula is C5H5ClN2, 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.

To a stirred solution of 4-chloropyridin-2-amine (8 g, 62.2 mmol) in acetonitrile (600 mL) at rt was added NBS (11.08 g, 62.2 mmol) in portions and the reaction was stirred for 14 h. The reaction mixture was concentrated under reduced pressure. The residue was reconstituted in ethyl acetate and water. The organics were extracted with ethyl acetate (3*50 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), and dried over sodium sulphate. The organics were concentrated under reduced pressure to afford 5-bromo-4-chloropyridin-2-amine as yellow solid (13 g, 99% yield) that was used without further purification in the next step. LCMS (ESI) m/e 207.0 [(M+H)+, calcd for C5H5BrClN2 206.9]; LC/MS retention time (method B): tR=0.8 min; 1H NMR (400 MHz, CDCl3) delta 8.17 (s, 1H), 6.63 (s, 1H), 4.59 (s, 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 19798-80-2, 4-Chloropyridin-2-amine.

Reference:
Patent; Bristol-Myers Squibb Company; Vrudhula, Vivekananda M.; Pan, Senliang; Rajamani, Ramkumar; Macor, John E.; Bronson, Joanne J.; Dzierba, Carolyn Diane; Nara, Susheel Jethanand; Karatholuvhu, Maheswaran Sivasamban; US2013/237555; (2013); A1;,
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Pyridine | C5H5N – PubChem

Related Products of 27048-04-0, 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. 27048-04-0, name is 6-Chloro-3-nitropyridin-2-amine, molecular formula is C5H4ClN3O2, 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.

A mixture of 2-amino-6-chloro-3-nitropyridine (1, 5.7 g, 32.8 mmol), water (4.5 mL), c-H2SO4 (1.26 mL) and H5IO6 (1.59 g) was stirred for 15 min at 95 C. Iodine (3.6 g) was added in portions. The reaction mixture was stirred for 1 h at 95 C., cooled to room temperature, poured into sat. aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc=3/2) to give compound 2 (8.7 g, 29.1 mmol, 88%). 1H NMR (DMSO-d6, 300 MHz) delta8.62 (s, 1H), 8.26 (brs, 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 27048-04-0, 6-Chloro-3-nitropyridin-2-amine.

Reference:
Patent; Benner, Steven A; Hoshika, Shuichi; (37 pag.)US10059737; (2018); B1;,
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Pyridine | C5H5N – PubChem

Reference of 1180132-17-5, 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 1180132-17-5 as follows.

Add to the microwave reaction flask7- [2-Chloro-5-fluoropyrimidin-4-yl) -5-fluoro-2,3-dihydro-1H-benzo [d] pyrrole [1,2-a] imidazole (100 mg, 0.33 mmol, Example 11 Preparation),5 – ((4-ethylpiperazin-1-yl) methyl) pyridin-2-amine(7 mg, 0.33 mmol, prepared in second step), sodium tert-butoxide (64 mg, 0.66 mmol), Pd2 (dba) 3 (30 mg, 0.033 mmol)XantPhos (38 mg, 0.066 mmol) and anhydrous 1,4-dioxane (5 mL).The mixture was microwave reacted at 150 C for 1 hour.Cooled to room temperature, extracted with water (10 mL), and ethyl acetate (40 mL x 3).The organic phases were combined, washed with saturated sodium chloride solution (40 mL x 2), dried over anhydrous sodium sulfate,Filtered, concentrated under reduced pressure. The residue was purified by column chromatography (DCM / MeOH = 10: 1)The resulting residue was purified to give the title compound (15 mg, yellow solid)Yield 9.3%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1180132-17-5, its application will become more common.

Reference:
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 944896-42-8, 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 944896-42-8, name is 6-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

[Step a] To a mixed solution of compound 1 (210 mg, 533 mumol) obtained in Reference Example 65, Step b, in dioxane (4.00 mL) and water (500 muL) were added potassium carbonate (170 mg, 1.23 mmol), compound 2 (, 100 mg, 415 mumol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (30 mg, 42.3 mumol), and the mixture was heated in a nitrogen atmosphere under microwave radiation at 150C, and stirred for 1 hr. The reaction solution was allowed to cool to room temperature, 1 M-hydrochloric acid (3.5 mL) was added, and the mixture was extracted with a tetrahydrofuran and ethyl acetate mixed solution (1:1). The aqueous layer was further extracted with a tetrahydrofuran and chloroform mixed solution (1:1), and the organic layers were combined, washed with saturated brine, and concentrated. The residue was subjected to solid phase extraction purification with a cation exchange resin column (Waters, PoraPak, RxnCX), and the obtained solid was suspended and washed in ethyl acetate (2.00 mL) to give compound 3 (70.0 mg, 39.4%).

According to the analysis of related databases, 944896-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; TAKAHASHI, Taichi; UMINO, Akinori; IIJIMA, Daisuke; TAKAMATSU, Hisayuki; (173 pag.)EP3135667; (2017); A1;,
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