Tag: M.W:200-300

Electric Literature of 24207-22-5 ,Some common heterocyclic compound, 24207-22-5, molecular formula is C7H8BrNO, 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.

[0125] 2-Bromo-3-methoxy-6-methylpyridine (XXXXV) 760 mg (3.76 mmol) was dissolved in 15 ml of water, and to the resulting solution was added potassium permanganate (KMnO4) (1.49 g, 9.40mmol) and the mixture was heated at 80 C for 3 hrs. After TLC was conducted, pH was adjusted to 4 with 10% hydrochloric acid (HCl) and filtration was conducted with celite. The filtrate was extracted with 50 ml of ethylacetate (EA). The organic layer was treated with magnesium sulfate (MgSO4) and filtered, and the solution was concentrated to give the title compound as a white solid (665 mg, 2.87 mmol, 75 %) without purification. 1H NMR (400 MHz, DMSO-d6) delta 13.22 (s, OH), 8.05 (d, J = 8.0 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 4.02 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24207-22-5, its application will become more common.

Reference:
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211532-15-8 , The common heterocyclic compound, 1211532-15-8, name is 6-Methoxy-5-(trifluoromethyl)nicotinic acid, molecular formula is C8H6F3NO3, 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.

Preparation Example 4 To a mixture of 6-methoxy-5-(trifluoromethyl)nicotinic acid (7.8 g) and dichloromethane (80 mL) were added N,O-dimethylhydroxylamine hydrochloride (4.3 g), WSCD.HCl (9.5 g), and N,N-diisopropylethylamine (30 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure, and to the residue were added ethyl acetate and water, followed by stirring for 30 minutes. The organic layer was separated, the aqueous layer was extracted with ethyl acetate, and the organic layer was combined, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain N,6-dimethoxy-N-methyl-5-(trifluoromethyl)nicotinamide (5.0 g) as an oil.

The synthetic route of 1211532-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; KOIKE, Takanori; NEGORO, Kenji; TANAKA, Hiroaki; MAEDA, Jun; YOKOYAMA, Kazuhiro; TAKAMATSU, Hajime; (146 pag.)EP3153511; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17570-98-8, 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.17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, molecular weight is 280.95, as common compound, the synthetic route is as follows.

EXAMPLE 1a; [(methylethyl)sulfonyl](trans-4-{[(4-(2-pyridyl)(1,3-thiazol-2-yl))amino]methyl}cyclohexyl)amine; N-({[(trans-4-{[(methylethyl)sulfonyl]amino}cyclohexyl)methyl]amino}thioxomethyl)amide (0.60 g, 2.0 mmol) was added to a stirred solution of 2-bromo-1-(2-pyridyl)ethan-1-one hydrobromide (0.57 g, 2.0 mmol) in EtOH (20 mL) at rt followed by the addition of DIEA (1.05 mL, 6.0 mmol). The reaction mixture was heated at reflux for 4 h, cooled to rt, and concentrated in vacuo. The resultant residue was re-dissolved in CHCl3 and washed successively with aqueous citric acid, water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (60% EtOAc in Hexanes) to afford the desired product as a tan colored solid (0.56 g, 69%). 1H NMR (CDCl3) delta 8.58 (d, 1H, J=4.8 Hz), 7.89 (dt, 1H, J=7.6 and 1.2 Hz), 7.71 (td, 1H, J=7.8 and 2.0 Hz), 7.17 (td. 1H, J=4.8 and 1.2 Hz), 5.25 (br s, 1H), 3.85 (d, 1H, J=8.4 Hz), 3.25 (br m, 1H), 3.18 (t, 2H, J=6.4 Hz), 2.14 (dt, 2H, J=12.0 and 1.2 Hz), 2.19 (br, d, 2H, J=12.8 Hz), 1.62 (br m, 3H), 1.38 (d, 6H, J=6.8 Hz), 1.25 (dq, 2H, J=12.8 and 1.6 Hz). LC-MS m/e: 395 (M+H)+; tR=2.14 min (Method-A).

Statistics shows that 17570-98-8 is playing an increasingly important role. we look forward to future research findings about 2-(Bromoacetyl)pyridine hydrobromide.

Reference:
Patent; Jubian, Vrej; Packiarajan, Mathivanan; Jimenez, Hermogenes; Reinhard, Emily; US2006/293341; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84199-61-1, 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. 84199-61-1, name is 3-Acetyl-2-bromopyridine, molecular formula is C7H6BrNO, 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.

General procedure: To a 200 mL round bottle flash was added sodium tert-butoxide (1.3equiv), followed by the addition of 50mL anhydrous THF, the mixture was stirred until all base was dissolved. Methyltriphenylphosphonium iodide (1.2equiv) was added in one port and the heterogeneous solution was stirred at rt for 30min. Pyridyl ketones (1.0equiv) were added slowly and the mixture was stirred at rt overnight. The mixture was quenched with water and extracted with ether twice. The combined organic layer was dried (MgSO4) and filtered, concentrated to provide some oil mixed with powder. The crude material was then distilled by Kugelrohr apparatus at 10mBar with temperature ranging from 50 to 100C to afford the product as colorless liquid. Characterization of unreported 1d, 1f is listed below:

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 84199-61-1, 3-Acetyl-2-bromopyridine.

Reference:
Article; Lian, Yajing; Burford, Kristen; Londregan, Allyn T.; Tetrahedron; vol. 71; 50; (2015); p. 9509 – 9514;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 183208-34-6 ,Some common heterocyclic compound, 183208-34-6, molecular formula is C7H5BrN2O, 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 mixture of 5-bromo-7-azaoxindole (213 mg, 1 mmol) in dimethylsulfoxide (1 ml) and ethanol (5 ml) in Parr bomb were added triethylamine (0.31 ml, 2.25 mmol), palladium acetate (33.7 mg, 0.15 mmol), and 1,3-(bisdiphenylphosphino)propane (61.9 mg, 0.15 mmol). Carbon monoxide gas (40 atm) was applied and the reaction mixture was heated at 95 C. for 18 hours with vigorously stirring. The reaction mixture was diluted with diethyl ether (50 ml) and washed with water (10 ml). The aqueous layer was thoroughly extracted with diethyl ether. The combined organic layers were dried over anhydrous MgSO4, filtered and evaporated under vacuum to give crude product. Trituation of the crude product with methanol yielded 5-(carboethoxy)-7-azaoxindole as a tan solid (53 mg, 25.7%). 1H NMR (DMSO-d6): delta 11.39 (s, 1H), 8.62 (s, 1H), 7.95 (s, 1H), 4.27 (q, 2H, J=7 Hz), 3.59 (s, 2H), 1.28 (t, 3H, J=7 Hz). MS (-ve APCl): 205 (4, 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. 183208-34-6, 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxo Wellcome Inc.; US6350747; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 944900-06-5 ,Some common heterocyclic compound, 944900-06-5, molecular formula is C7H3ClF3NO, 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.

2-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde 8 (11.96 g, 57.1 mmol) was added to a solution of N-Boc ethylenediamine (5.83 mL, 58.2 mmol) and Na2SO4 (50 g) in CH2Cl2 (400 mL) at room temperature, and the reaction mixture was stirred for 17 h. After the reaction mixture was concentrated, the residue was purified by silica gel column chromatography (hexane/AcOEt = 3:2) to provide the imine (13.87 g, 69%) as a yellow oil. 1H NMR (CDCl3) delta: 8.67 (1H, s), 8.53 (1H, d, J = 7.8 Hz), 7.68 (1H, d, J = 7.8 Hz), 4.79 (1H, br s), 3.83 (2H, t, J = 5.5 Hz), 3.50 (2H, q, J = 5.7 Hz), 1.44 (9H, s). A solution of allylmagnesium bromide in Et2O (0.7 M, 60 mL, 42 mmol) was added to a solution of the imine (13.44 g, 38.2 mmol) in THF (150 mL) under N2 atmosphere at 0 C, and the mixture was stirred at the same temperature for 45 min. Then, the reaction mixture was diluted with H2O (200 mL), extracted with AcOEt (400 mL), washed with brine, dried (Na2SO4), concentrated. The residue was purified by silica gel column chromatography (hexane/AcOEt = 7:3) to provide 9 (10.91 g, 73%) as a yellow oil. 1H NMR (CDCl3) delta: 8.12 (1H, d, J = 8.2 Hz), 7.64 (1H, d, J = 7.8 Hz), 5.82-5.71 (1H, m), 5.17-5.11 (2H, m), 4.72 (1H, br s), 4.21-4.10 (2H, m), 3.21-3.14 (2H, m), 2.65-2.59 (1H, m), 2.57-2.52 (1H, m), 2.47-2.41 (1H, m), 2.24-2.16 (1H, m), 1.44 (9H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,944900-06-5, its application will become more common.

Reference:
Article; Matsufuji, Tetsuyoshi; Shimada, Kousei; Kobayashi, Shozo; Ichikawa, Masanori; Kawamura, Asuka; Fujimoto, Teppei; Arita, Tsuyoshi; Hara, Takashi; Konishi, Masahiro; Abe-Ohya, Rie; Izumi, Masanori; Sogawa, Yoshitaka; Nagai, Yoko; Yoshida, Kazuhiro; Abe, Yasuyuki; Kimura, Takako; Takahashi, Hisashi; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 89 – 104;,
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. 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate. A new synthetic method of this compound is introduced below., Computed Properties of C12H16N2O4

Compound 2E (2.5 g, 9.91 mmol, 1.00 equiv) and CaC12 (1.65 g) were dissolved in EtOH (30 mL). The solution was cooled to 0C then NaBH4 (1.13 g, 29.87 mmol, 3.01 equiv) was gradually added. The solution was left under agitation overnight atambient temperature then the reaction was halted with the addition of water (50 mL). The mixture was extracted three times with 20 mL of EtOAc. The organic phases were combined, washed twice with 20 mL of NaC1 (sat.) then dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 2.0 g (90 %) of compound 2F in the form of a colourless solid.

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, 639091-75-1, Methyl 2-(Boc-amino)isonicotinate.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174062; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22282-70-8, 2-Fluoro-4-iodopyridine, 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, 22282-70-8, blongs to pyridine-derivatives compound. COA of Formula: C5H3FIN

A mixture of 2-fluoro-4-iodopyridine (10.00g, 43.50mmol), ammonium hydroxide (10mL) in DMSO (20mL) was stirred at 100 C for 40 hours. H2O (100mL) was added to the reaction mixture and the precipitate was filtered to afford the compound 10a as a brown solid (8.62g, 90%). MS: 221 (M+H) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-70-8, its application will become more common.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; MA, Cunbo; GAO, Panliang; CHU, Jie; WU, Xinping; WEN, Chunwei; KANG, Di; BAI, Jinlong; PEI, Xiaoyan; (82 pag.)WO2017/211303; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1241752-31-7, 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 1241752-31-7, name is 5-Bromo-2-ethoxy-3-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-bromo-2-ethoxy-3-methoxy-pyridine (1 .70 g, 7.33 mmol) in N,Ndimethylformamide (10 mL) was added zinc cyanide (860 mg, 7.33 mmol, 464 iL), and tetrakis(triphenylphosphine)palladium(0) (847 mg, 733 imol, 0.10 eq), the mixture was degassed with nitrogen for three times. The resulting mixture was stirred at 110 00 for 12 h under nitrogen atmosphereand then poured into water (30 mL). The mixture was then extracted with dichloromethane (50 mL x 3). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide the crude product purified by chromatography (silica, petroleum ether ethyl acetate 50:1 Rt 0.6). The title compound, 6-ethoxy-5-methoxy-pyridine-3-carbonitrile was isolated as a white solid (820 mg, 4.60 mmol, 63 %) 1H NMR (400MHz, METHANOL-d4) O 8.08 (d,J1.8 Hz, 1H), 7.49(d, J1.8 Hz, 1H), 4.48 (q, J7.1 Hz, 2H), 3.92 -3.88 (m, 3H), 1.42(t, J7.1 Hz, 3H)

According to the analysis of related databases, 1241752-31-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7477-10-3, Adding some certain compound to certain chemical reactions, such as: 7477-10-3, name is 6-Chloro-5-nitronicotinic acid,molecular formula is C6H3ClN2O4, 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 7477-10-3.

General procedure: A solution of compound 4 and different primary and secondary amines were stirred at rt for 1h, followed by extraction with EtOAc. The extract was then washed with 1N HCl, water, and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography (hexane/EtOAc=2:1) to give product 6 as a solid. 4.2.4.2 6-((3-Methoxyphenyl)amino)-5-nitronicotinic acid (6b) Procedure A was used with compound 5 (300 mg, 1.5 mmol) and m-anisidine (370 mg, 3.0 mmol) to afford product 6b as a yellow solid (258 mg, 53%). 1H NMR (300 MHz, CDCl3) delta: 8.90 (s, 1H), 8.73 (s, 1H), 7.38 (t, J = 7.8 Hz, 1H), 7.08 (d, J = 7.8 Hz, 1H), 6.72 (d, J = 7.8 Hz, 1H), 6.52 (s, 1H), 3.83 (s, 3H). ESI-MS: m/z (288, MH-).

According to the analysis of related databases, 7477-10-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Chao; Yang, Su Hui; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kyung-Tae; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 985 – 995;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem