Category: pyridine-derivatives

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. SDS of cas: 85838-94-4

To a solution of N-Boc-1,2,3,6-tetrahydropyridine (3.63 g, 21.0 mmol) in 40 niL of dichloromethane was added 3-chloroperoxybenzoic acid (2.75 g, 15.0 mmol). The reaction was stirred at room temperature for 4 h, then washed 3x with saturated aqueous potassium carbonate and once with brine. The solution was dried over sodium sulfate, filtered, and concentrated in vacuo to provide crude fert-butyl 7-oxa-3-azabicyclo[4,1.0]heptane-3-carboxylate that gave a proton NMR spectra consistent with theory.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; CHANG, Ronald, K.; GRESHOCK, Thomas, J.; WO2011/25851; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 614750-81-1, 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. 614750-81-1, name is [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde. A new synthetic method of this compound is introduced below.

(b) 1-(6-Methyl-pyridin-2-yl)-2-[1,2,4]triazolo[1,5-a]pyridin-6-yl-ethanone To a solution of [1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde (3 g, 20 mmol; see subpart (a) above) and [(6-methyl-pyridin-2-yl)-phenylamino-methyl]-phosphonic acid diphenyl ester (8.8 g, 20 mmol; prepared from 6-methyl-pyridine-2-carboxaldehyde (Aldrich-Sigma, St. Louis, Mo.) according to Tetrahedron Lett. 39:1717-1720 (1998)) in a mixture of THF (40 mL) and iPrOH (10 mL) was added Cs2CO3 (8.6 g, 26 mmol) and the mixture was stirred at room temperature for overnight. A solution of 3N HCl (30 mL) was added dropwise to the above mixture and stirred for 1 hour. It was then diluted with MTBE (methyl t-butyl ether) and extracted with 1N HCl twice. The aqueous extracts were neutralized with ca. 50percent KOH until pH 7-8 was reached and precipitates formed. The precipitates were collected, washed with water, and dried to yield 1-(6-methyl-pyridin-2-yl)-2-[1,2,4]triazolo[1,5-a]pyridin-6-yl-ethanone as an off white solid (2.9 g). The filtrates were extracted with EtOAc and dried over MgSO4 and concentrated. The residue was recrystallized with iPrOH/H2O to yield more desired product (0.6 g). ESP+, m/e 253. 1H NMR (CDCl3, 300 MHz), delta 8.6 (s, 1H), 8.29 (s, 1H), 7.87 (d, 1H), 7.72 (t, 1H), 7.70 (d, 1H), 7.53 (dd, 1H), 7.36 (d, 1H), 4.61 (s, 2H), 2.66 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,614750-81-1, [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Lee, Wen-Cherng; Sun, Lihong; Shan, Feng; Chuaqui, Claudio; Zheng, Zhongli; Petter, Russell C; US2006/63809; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52718-95-3, Adding some certain compound to certain chemical reactions, such as: 52718-95-3, name is Methyl 2-bromonicotinate,molecular formula is C7H6BrNO2, 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 52718-95-3.

Intermediate [1-B] (1.5 eq), methyl-2-bromoicotinate (1.1 eq), CuI (0.03 g), K2CO3 (2.0 eq), and L-Proline (0.04 eq) were dissolved in toluene (0.1 M) and stirred at a temperature of 130 i for 12 hours. After the reaction mixture was cooled to room temperature, and an organic layer was dried by using magnesium sulfate and concentrate, and column chromatography was used to obtain Intermediate [1-C] (yield: 59%).

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. 52718-95-3, Methyl 2-bromonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Samsung Display Co., Ltd.; KANG, Sunwoo; JEON, Sangho; CHO, Youngmi; (80 pag.)US2020/168817; (2020); A1;,
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. 104408-24-4, name is 6-Hydrazinylnicotinonitrile, molecular formula is C6H6N4, 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. Safety of 6-Hydrazinylnicotinonitrile

General procedure: To a solution of 2-hydrazinylpyridine (2, 0.5?mmol) in EtOH (5?mL) was added the corresponding isothiocyanate (3, 0.6?mmol) slowly at room temperature. After the total consumption of the substrate 2 (indicated by TLC), the reaction mixture was treated with iodine (140?mg, 0.55?mmol) and K2CO3 (138?mg, 1?mmol) in sequence, and then stirred at room temperature until TLC indicated the disappearance of the addition intermediate 4. Upon the completion of the reaction, it was quenched with 5% Na2S2O3 (5?mL), diluted with brine (10?mL) and then extracted with CH2Cl2 (enriched 5% MeOH, 4?*?10?mL). The combined organic layer was dried over anhydrous Na2SO4, concentrated, and then purified through silica gel column chromatography using a mixture of EtOAc/petroleum ether (PE) or MeOH/EtOAc as the eluent to afford the product 1.

With the rapid development of chemical substances, we look forward to future research findings about 104408-24-4.

Reference:
Article; Jiao, Shufeng; Wang, Zhen; Zhao, Qiongli; Yu, Wenquan; Chang, Junbiao; Tetrahedron; vol. 74; 24; (2018); p. 3069 – 3073;,
Pyridine – Wikipedia,
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. 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below., Quality Control of 2-Oxo-1,2-dihydropyridine-3-carboxylic acid

To a solution of 2-hydroxynicotinic acid 1 (18.98 g, 0.136 mmol) in glacial acetic acid was added bromine (8.4 ml, 0.163 mmol). The reaction mixture was stirred at 80 C overnight and monitored by TLC to confirm its completion. The reaction mixture was then evaporated in vacuo and the resulted precipitate was collected, washed with cold water and filtered to furnish the compound 2 in good yields. (22.7, 76.6%). 1H-NMR (300 MHz, CDCl3) delta 8.25 (d, J = 2.4 Hz, 1H), 8.34 (d, J = 2.4 Hz, 1H), 13.8 (brs, 1H).

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, 609-71-2, 2-Oxo-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Article; Liu, Linyi; Li, Xinyu; Cheng, Yu; Wang, Lianjian; Yang, Huizhu; Li, Jiurong; He, Siying; shuangjie Wu; Yin, Qianqian; Xiang, Hua; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 304 – 316;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 159991-07-8, 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. 159991-07-8, name is (4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate. A new synthetic method of this compound is introduced below.

Example 210; 3,3-bis(4-fluorophenyl)-l-(2-oxo-2-{(4aS,7aS)-l-[3-(trifluoromethyl)benzyl]octahydro-6H-pyrrolo [3,4-6] pyridin-6-yl}ethyl)pyrrolidin-2-one; Example 210A; 3,3-bis(4-fluorophenyl)-l-(2-oxo-2-((4aS,7aS)-tetrahydro-lH-pyrrolo[3,4-6]pyridin- 6(2H,7H,7aH)-yl)ethyl)pyrrolidin-2-one; To a solution of 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-l-yl)acetic acid (Example 58D) (0.331 g, 1 mmol) and (4aS,7aS)-tert-butyl octahydro-lH-pyrrolo[3,4-6]pyridine-l- carboxylate (Example 50 B) (0.226 g, 1 mmol) in methylene chloride (20 mL) was added O- (7-azabenzotriazol-l-yl)-Lambda/,Lambda/,Lambda/’,Lambda/’-tetramethyluronium hexafluorophosphate (0.38g, 1 mmol) and diisopropylethylamine (0.45 mL). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with methylene chloride, and then washed with 1 iVEtaCl, water, 1 iVNaOEta, and water. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The obtained residue was purified by silica gel chromatography eluting with ethyl acetate to yield the t-butoxycarbonyl-protected title compound. That material was dissolved in dichloromethane (10 mL) and treated with trifluoroacetic acid (2 mL) for 1 hour at room temperature. The reaction mixture was concentrated and partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The organic layer was separated, dried over MgSO4 and concentrated to give the title compound. 1H NMR (300 MHz, CDCl3) delta ppm 7.35 (m, 4 H), 7.00 (m, 4 H), 4.25 (dd, 1 H), 3.96 (t, J=16.78 Hz, 1 H), 3.47 (m, 7 H), 3.00 (m, 1 H), 2.78 (m, 2 H), 2.63 (m, 1 H), 2.27 (m, 1 H), 1.72 (m, 2 H) 1.45 (m, 2H); MS (ESI+) m/z 440 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,159991-07-8, (4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT LABORATORIES; BHATIA, Pramila, A.; DOHERTY, George, A.; DRIZIN, Irene; MACK, Helmut; PERNER, Richard, J.; STEWART, Andrew, O.; ZHANG, Qing Wei; WO2010/39947; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5345-47-1, 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.5345-47-1, name is 2-Aminonicotinic acid, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

Example 1.3: Preparation of (4-(2,4-Difluorophenethyl)piperazin-l-yl)(imidazo[l,2- alpha]pyridin-8-yl)methanone (Compound 3).Step A: Preparation of Imidazo[l,2-alpha]pyridine-8-carboxylic Acid.To a mixture of 2-aminonicotinic acid (0.6906 g, 5.00 mmol) in acetonitrile (20 mL) was added bromoacetaldehyde dimethyl acetal (0.591 mL, 5.00 mmol). The resulting slurry was heated at 150 0C under microwave irradiation for 2 h. The resulting precipitate was filtered off and washed with acetonitrile and hexane to afford the title compound (0.924 g) as a grey solid.

The chemical industry reduces the impact on the environment during synthesis 5345-47-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS INC.; WO2009/23253; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65515-28-8, Methyl 2,6-dichloronicotinate, 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: 65515-28-8, blongs to pyridine-derivatives compound. SDS of cas: 65515-28-8

5.58 g (111 mmol) of hydrazine · monohydrate was added to a mixed solution of 11.5 g (55.8 mmol) of 2,6-dichloronicotinic acid methylate and 150 ml of dioxane at room temperature. After the addition was completed, the reaction mixture was stirred at room temperature for 18 hours. After completion of the stirring, water was added to stop the reaction, and the solvent in the reaction solution was distilled off under reduced pressure. The precipitated solid was washed with water and collected by filtration to obtain 10.7 g of the objective compound as a yellow solid.

The synthetic route of 65515-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nissan Chemical Industries, Ltd.; Nakaya, Kiyohiko; Tanima, Daisuke; Inaba, Masamitsu; MiyaKaku, Hiroki; Furuhashi, Takayuki; Maeda, Kanenari; Ikeda, Eitatsu; (181 pag.)JP2018/76298; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 37669-64-0 ,Some common heterocyclic compound, 37669-64-0, molecular formula is C6H6BrNO, 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.

To a solution of (5-bromo-pyridin-3-yl)-methanol, (0.500 g, 2.68 mmol) DCM (10 mL) was added thionyl chloride (0.5 mL) and the resulting solution was stirred at room temperature for 2 h. The reaction mixture was quenched by the addition of water and extracted into DCM. The organic extracts were washed with brine filtered and concentrated under reduced pressure to provide 3-bromo-5- chloromethyl-pyridine (0.45 g, 82 %), which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,37669-64-0, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JOHNSON, James A.; LLOYD, John; FINLAY, Heather; JIANG, Ji; NEELS, James; DHONDI, Naveen Kumar; GUNAGA, Prashantha; BANERJEE, Abhisek; ADISECHAN, Ashokkumar; WO2011/28741; (2011); A1;,
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. 56622-54-9, name is (6-Methylpyridin-3-yl)methanamine, molecular formula is C7H10N2, 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. Safety of (6-Methylpyridin-3-yl)methanamine

[0340] To a stirred solution of compound XI (0.15 g, 0.42 mmol, leq) in CH2C12: DMF (1:5, 20 mL) were added DIPEA (0.22 mL, 1.2 mmol, 3 eq) and HATU (0.2 g, 0.54 mmol, 1.3 eq) and the resulting mixture was stirred at 0 C for 15 mm. To the mixture was added C-(6-methyl-pyridin-3-yl)-methylamine (0.13 g, 0.85 mmol, 2 eq) and the resulting mixture allowed to stir at 23 C for another 16 h. From the mixture, solvent was removed in vacuo, the residue was diluted with EtOAc and washed with saturated aqueous sodium bicarbonate solution, aqueous ammonium chloride solution and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The crude product was purified by silica gel (230-400 mesh) column chromatography eluting with 0-10% methanol/CH2C12 to obtain the title compound (30 mg, 16%) as an off white solid. 1H NMR (DMSO-d6) oe 9.37 (t, 1H, J = 6 Hz), 9.10 (d, 1H, J = 1 Hz), 8.42 (d, 1H, J = 2 Hz), 7.90 (d, 1H, J = 1 Hz), 7.84 (s, 1H), 7.68 (d, 1H, J = 1 Hz), 7.63 (dd, 1H, J = 2, 8 Hz), 7.43 (d, 1H, J= 4 Hz), 7.22 (d, 1H, J = 8 Hz), 7.03 (d, 1H, J = 3 Hz), 6.35 (s, 1H), 4.48 (d, 2H, J = 6 Hz),2.62 (q, 2H, J= 8Hz), 2.55 (s, 3H), 2.50 (s, 3H), 1.11 (t, 3H, J= 8Hz). LCMS: mlz = 457.0[M+Hj , RT = 3.21 minutes, (Program P1, Column Y).

With the rapid development of chemical substances, we look forward to future research findings about 56622-54-9.

Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott; VENKATESAN, Aranapakam; PRIESTLEY, Tony; KUNDU, Mrinal; SAHA, Ashis; WO2015/95128; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem