Category: pyridine-derivatives

Reference of 72093-07-3, 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.72093-07-3, name is 5-Chloro-2-methylpyridine, molecular formula is C6H6ClN, molecular weight is 127.57, as common compound, the synthetic route is as follows.

To a solution of 5-chloro-2-methylpyridine (Step A, 1.1 g, 8.7 mmol) in 15 mL anhydrous ether was added phenyl lithium (1.8 M in cyclohexane/ether, 7.2 mL, 13 mmol) at 0C, and the reaction was stirred at room temperature for 30 min. The resulting mixture was cooled back to 0C, and was added (LR, 2R)-1-phenylpropylene oxide (2.3 g, 17 mmol), and the reaction was allowed to warm to room temperature overnight. The reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over anhydrous MGS04, filtered, and concentrated to dryness, and the residue was purified by flash column chromatography on silica gel eluted with 10 to 40% EtOAc in hexane to afford the title compound. 1H NMR (500 MHz, CD30D) : 8 8.28 (d, 1H), 7.59 (dd, 1H), 7.25-7. 12 (m, 5H), 7.05 (d, 1H), 4.03 (m, 1H), 3.29 (dd, 1H), 3.19 (dd, 1H), 3.12 (m, 1H), 1.12 (d, 3H).

Statistics shows that 72093-07-3 is playing an increasingly important role. we look forward to future research findings about 5-Chloro-2-methylpyridine.

Reference:
Patent; MERCK & CO., INC.; WO2004/48317; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1121-60-4, 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. 1121-60-4, name is Picolinaldehyde. A new synthetic method of this compound is introduced below.

General procedure: To a mixture of 1,2-phenylenediamines (1.0 mmol) andaldehydes (1.1 mmol) in ethanol, 25 mol % of Ag2CO3/Celite (3 mL) was added. The resulting mixture was stirredat 70 C for 3 h. After this time, the reaction mixture wasdiluted with ethanol (50 mL) and the catalyst was separatedby filtration. Water was then added to the organic layer, andthe products were filtered and washed with water. All of theproducts are known compounds and characterized easily bycomparison with melting point, IR, [1-6] H NMR spectraldata reported in literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1121-60-4, Picolinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Soleimani, Ebrahim; Khodaei, Mohammad Mehdi; Yazdani, Hossein; Saei, Parisa; Zavar Reza, Javad; Journal of the Iranian Chemical Society; vol. 12; 7; (2015); p. 1281 – 1285;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 24517-64-4, Adding some certain compound to certain chemical reactions, such as: 24517-64-4, name is 2-Amino-3-cyanopyridine,molecular formula is C6H5N3, 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 24517-64-4.

8.1 Compound 9: 2-Aminonicotinonitrile 8 (100 g, 0.839 mol) was dissolved in HOAc (800 mL) . To the solution was added Na2C03 (88.97 g, 0.839 mol). Then, Br2 (46.4 mL, 0.923 mol) was added dropwise. The reaction mixture was stirred at room temperature for 50 min. To the mixture was added water (600 mL) . The mixture was cooled to about 5C. The precipitate thus formed was collected by filtration and dried to give compound 9 (207 g, 96%) .

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. 24517-64-4, 2-Amino-3-cyanopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; WO2013/29548; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 76006-08-1, 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. 76006-08-1, name is 5-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, 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 solution of 5-chloro-1H-pyrazolo[3,4-c]pyridine (15 g, 1 equiv) in DMF (150 mL) was added iodine (37.2 g, 1.5 equiv) and potassium hydroxide (13.7 g, 2.5 equiv) at 0 C. The reaction mixture was stirred at room temperature for 12 h and then diluted with 10% aqueous sodium thiosulfate (250 mL) and extracted with EtOAc. The combined organic extracts were washed with brine and then dried. The obtained solid (15 g) was slurried with MTBE, filtered and dried.

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 76006-08-1, 5-Chloro-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 154237-70-4, 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. 154237-70-4, name is 4-Bromo-3-cyanopyridine. A new synthetic method of this compound is introduced below.

3-Cyano-4-(phenylethynyl)pyridine (35). Copper(l) iodide (9.6 mg, 0.05 mmol), bis- (triphenylphosphine)palladium(ll) dichloride (29 mg, 0.025 mmol) and sodium ascorbate (9.9 mg, 0.05 mmol) were placed in a flask, which was degassed and filled with argon. Triethylamine (5.0 mL) was added, followed by 4-bromo-3-cyanopyridine 34 (92 mg, 0.5 mmol) in tetrahydrofuran (5.0 mL). The mixture was stirred at 40C for 30 min. Phenylethyne (76.5 mg, 0.75 mmol) was added and the mixture was stirred at 40C for 10 h. Evaporation and chromatography (petroleum ether / ethyl acetate 3: 1) gave 3-cyano-4-(phenylethynyl)pyridine 35 (80 mg, 78%) as an off-white powder: mp 74-75C (lit.91 85-87C); IR vmax 2222 (C?N), 2150 (C?C), 1582 (C=CAr), 1495 (C=N) cm”1; 1H NMR (CDCI3) delta 7.39-7.43 (3 H, m, Ph 3,4,5-H3), 7.45 (1 H, d, J = 5.2 Hz, 5-H), 7.63 (2 H, d, J = 8.2 Hz, Ph 2,6-H2), 8.75 (1 H, d, J = 5.2 Hz, 6-H), 8.87 (1 H, s, 2-H); 13C NMR (CDCI3) (HSQC / HMBC) delta 83.50 (ethyne 2-C), 101.29 (ethyne 1-C), 1 1.74 (4-C), 1 15.54 (C?N), 120.76 (Ph 1-C), 125.06 (5-C), 128.59 (Ph 3,5-C2), 130.28 (Ph 4- C), 132.38 (Ph 2,6-C2), 134.87 (3-C), 152.40 (2-C), 152.68 (6-C); MS m/z 227.0569 (M + Na)+ (C14H8N2Na requires 227.0585).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,154237-70-4, its application will become more common.

Reference:
Patent; UNIVERSITY OF BATH; THREADGILL, Michael David; LLOYD, Matthew David; THOMPSON, Andrew Spencer; NATHUBHAI, Amit; WOOD, Pauline Joy; PAINE, Helen Angharad; KUMPAN, Ekaterina; SUNDERLAND, Peter Thomas; CHUE YEN WOON, Esther; WO2014/87165; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 128071-75-0 ,Some common heterocyclic compound, 128071-75-0, molecular formula is C6H4BrNO, 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.

1. (2-Bromo-3-pyridyl)methanol; To a 2 L round bottom flask (fitted with stir bar, under nitrogen and at 0 C.) containing 2-bromo-3-pyridine-carboxaldehyde (22.15 g, 119.08 mmol) and methanol (200 mL), is added sodium borohydride (1.35 g, 35.72 mmol) in three portions. After 1 h at 0 C. water (200 mL) is added and the reaction is concentrated under reduced pressure to remove the methanol. The resulting residue is dissolved in ethyl acetate and washed with water (200 mL). The organic extraction is washed with brine, dried over magnesium sulfate, filtered and concentrated to afford 22 g of (2-bromo-3-pyridyl)methanol as a white solid. MS (m/z): 188 (M+1), 190 (M+3).

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. 128071-75-0, 2-Bromonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; US2011/118251; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13362-26-0, name is Ethyl 2-aminonicotinate, the common compound, a new synthetic route is introduced below. name: Ethyl 2-aminonicotinate

Example 16 Synthesis of 2-chloro-imidazo[1,2-a]pyridine-8-carboxylic acid (Compound No. 1-135) A mixture of diethyl bromomalonate (26 ml) and ethyl 2-aminonicotinate (13.3 g) was allowed to react at 80-90 C. for 6 hours under nitrogen atmosphere. After completion of the reaction, the mixture was cooled to room temperature, and acetone (100 ml) was added thereto. The precipitated crystals were collected by filtration, affording 3,8-diethoxycarbonyl-2-hydroxy-imidazo[1,2-a]pyridine hydrobromide (9.98 g, yield 34.8%). A mixture of the crystals (6.6 g) in phosphorus oxychloride (30 ml) was reacted at 160 C. for 2 hours in a pressure reaction vessel. After completion of the reaction, excess phosphorus oxychloride was removed under reduced pressure. Ethanol was added to the residue, and the mixture was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: chloroform) to obtain 2-chloro-3,8-diethoxycarbonyl-imidazo-[1,2-a]pyridine (Compound No. 1-133) (2.2 g, yield 40.3%) as crystals of m.p. 105-106 C.

The synthetic route of 13362-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5498774; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 80194-68-9, 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 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

A solution of the carboxylic acid (0.3 mmol) in N,N-dimethylformamide (5 ml) was cooled to 0 C. Consecutively, 1 -hydro xybenzotriazole hydrate (52 mg, 0.38 mmol), 0-(benzotriazol-l- yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (143 mg, 0.38 mmol), (R)-3-(5-amino- 2-fluoro-phenyl)-3-methyl-[l,4]oxazepan-5-one hydrochloride (intermediate C13A) (74 mg, 0.27 mmol), and N-ethyldiisopropylamine (124 mg, 0.94 mmol) were added, and the mixture was stirred at 0 C for 10 minutes, then left at room temperature for 16 hours. For the workup, the reaction mixture was evaporated to dryness and the residue directly purified by chromatography on a Silicycle-Si-amine column using a gradient of heptane and ethyl acetate as the eluent.Intermediate C14AStarting from 3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid and (R)-3-(5-amino-2- fluoro-phenyl)-3-methyl-[l,4]oxazepan-5-one hydrochloride, the 3-chloro-5-trifluoromethyl- pyridine-2-carboxylic acid [4-fluoro-3-((R)-3-methyl-5-oxo-[ 1 ,4]oxazepan-3-yl)-phenyl] -amide was obtained as a light yellow foam. MS (ISP): m/z = 446.1 [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 80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A.; BANNER, David; GUBA, Wolfgang; HILPERT, Hans; HUMM, Roland; MAUSER, Harald; MAYWEG, Alexander, V.; NARQUIZIAN, Robert; POWER, Eoin; ROGERS-EVANS, Mark; ROMBACH, Didier; WOLTERING, Thomas; WOSTL, Wolfgang; WO2011/138293; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13091-23-1, name is 4-Chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 13091-23-1

Sodium carbonate (3.20 g, 30.27 mmol) and 4-fluorobenzylamine (2.14 ml, 18.92 mmol) were added to a solution of 4-chloro-3-nitropyridine (3.0 g, 18.92 mmol) prepared in Step 1 of Preparation 1 in 30 ml of anhydrous JV,./V-dimethylformamide and then the reaction mixture was stirred for 1 hour at 800C. The reaction mixture was diluted with a mixture of water (10 ml) and ethyl acetate (100 ml) and then washed with water (100 ml) twice. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure to give the titled compound as a yellow solid (3.01 g, 83.5%).[63] 1 Eta-NMR (CDCl ) delta 8.60(s, 1Eta), 7.29(m, 3Eta), 7.18(m, 2H), 6.70(d, IH), 5.20(s,2H)

The synthetic route of 13091-23-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; JANG, Sun-Young; WO2006/38773; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65515-28-8, 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. 65515-28-8, name is Methyl 2,6-dichloronicotinate. A new synthetic method of this compound is introduced below.

A 250 mL eggplant flask was sequentially charged with methyl 2,6-dichloronicotinate (8.24 g, 40 mmol), 4-bromophenol (6.92 g,40 mmol), and 50 mL of N, N-dimethylformamide for dissolving them. Triethylamine (7.2 mL, 52mmol) was added dropwise under stirring at room temperature, and after completion of the dropwise addition, triethylenediamine (672 mg, 6 mmol) was added. The mixture was stirred at room temperature for 4-5 hours and the solutionchanged from clear to turbid. Thin layer chromatography [V (petroleum ether) / V (ethyl acetate) = 6/1] detected thatmost of the raw material disappeared. Then, 1.30 mL of HOAc, 25 mL of isopropanol and 15 mL of ice water weresequentially added while the solution changed from turbid to clear, and stirred at room temperature for 0.5 hour. 40 mLof water was slowly dropwise added, and after completion of the dropwise addition, stirred at room temperature for 2hours. A large number of white solid precipitated and was filtered. The filter cake was washed with a mixed solution ofisopropyl alcohol / water = 1: 1 and dried under vacuum at 50 C for 8 hours to obtain 11.48 g of methyl 6-(4-bromophenoxy)-2-chloronicotinate as a solid, 83.92%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65515-28-8, its application will become more common.

Reference:
Patent; Shenyang Sunshine Pharmaceutical Co., Ltd.; ZHOU, Yunlong; CAI, Suixiong; WANG, Guangfeng; JIAO, Lingling; MIN, Ping; JING, Yu; GUO, Ming; (44 pag.)EP3275881; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem