Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 88579-63-9, 2,6-Dichloropyridine-4-methylamine, 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, name: 2,6-Dichloropyridine-4-methylamine, blongs to pyridine-derivatives compound. name: 2,6-Dichloropyridine-4-methylamine

Intermediate 1-2-46solution of intermediate 1 -1 -5 (3.07 g, 12.4 mmol) and 2,6-dichloro-4- (aminomethyl)pyridine (2 g, 1 1.3 mmol) in EtOH:EtOAc (1 :1 , 150 mL) was heated at reflux for 72h under Dean-Stark conditions with 4A molecular sieves. Concentrated and purified by silica chromatography to give the intermediate 1 -2-46 (2460 mg, 54%). 1 H-NMR (400 MHz ,DMSO-d6), Shift [ppm]= 1.81 (2H), 2.44 (2H), 2.69 (2H), 4.83 (2H), 7.20-7.28 (1 H), 7.35-7.44 (2H), 7.47-7.54 (2H), 7.56 (2H), 13.09 (1 H), 14.24 (1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88579-63-9, 2,6-Dichloropyridine-4-methylamine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; KLAR, Ulrich; BRIEM, Hans; HITCHCOCK, Marion; BAeRFACKER, Lars; EIS, Knut; SCHULZE, Volker; SIEMEISTER, Gerhard; BONE, Wilhelm; SCHROeDER, Jens; HOLTON, Simon; LIENAU, Philip; TEMPEL, Rene; SONNENSCHEIN, Helmut; BALINT, Jozsef; GRAUBAUM, Heinz; (577 pag.)WO2015/193339; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153813-70-8, 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 153813-70-8, name is 3-Nitroisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 11: Methyl 2- [(tert-butoxvcarbonyl) amino] -3-(3nitropyridin-4-yl) acrylate; Methyl [(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate (1.73 g, 5.82 mmol) was dissolved in dry THF (20 ml) and cooled to -78 C under nitrogen. Tetramethylguanidine (638 mg, 5.55 mmol) was added and the solution stirred at -78 C for a further 10 mins. A solution of 3-nitroisonicotinaldehyde (Intermediate 12,804 mg, 5.29 mmol) in dry THF (5ml) was added dropwise. The resulting deep red solution was stirred for 2hrs. at -78C, then poured into a mixture of ethyl acetate (100 ml) and water (50 ml). The organic layer was separated, washed with water (2 x 50 ml) and brine (25 ml), dried (MgS04) and evaporated under reduced pressure to give a yellow oil, which was purified by column chromatography (EtOAc: isohexane 1:1) to give methyl-2-[(tert-butoxycarbonyl)amino]-3-(3-nitropyridin-4- yl) acrylate as a 10: 1 mixture of Z/E isomers (1.57 g, 92%). ¹H NMR: 1.3 (s, 9H); 1.4 (s, 0.9H) ; 3.55 (s, 0.3H) ; 3.8 (s, 3H) ; 6.6 (s, O.IH); 7.2 (s, 1H); 7.25 (d, 0.1H); 7.5 (d, 1H); 8.75 (d, O.1H); 8.8 (s, 1.1H); 8.85 (d, 1H); 9.2 (s, O.1H); 9.25 (s, 1H); MS: 322.

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 153813-70-8, 3-Nitroisonicotinaldehyde.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/123685; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 56826-61-0, Adding some certain compound to certain chemical reactions, such as: 56826-61-0, name is (2-Methylpyridine-3-yl)methanol,molecular formula is C7H9NO, 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 56826-61-0.

Preparation of 2-methylnicotinaldehyde A mixture of (2-methylpyridin-3-yl)methanol (1.0 g, 8.12 mmol) in dichloromethane (10 mL) and manganese oxide (7.06 g, 81.2 mmol) was stirred at room temperature for sixty hours and then heated at 45 C. for 4 h. The reaction was filtered through celite and a plug of silica gel (5*7 cm) using ethyl acetate as eluent. The filtrate was then concentrated to give 2-methyl nicotinaldehyde as an oil (680 mg). 1H NMR (400 MHz, CDCl3) delta 10.32 (s, 1H), 8.67 (dd, 1H), 8.09 (dd, 1H), 7.31 (dd, 1H), 2.88 (s, 3H).

According to the analysis of related databases, 56826-61-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2008/85887; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1227502-35-3, 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 1227502-35-3 as follows.

5-bromo-3-(hydroxymethyl)pyridin-2(lH)-one (34.1 mg, 0.167 mmol) was stirred with iodomethane (30.5 mu, 0.201 mmol) and potassium carbonate (115 mg, 0.836 mmol) in DMF (557 mu) in a 2-dram vial containing a Teflon-coated stir bar at room temperature for 1 h. Additional DMF (1.0 mL) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 19 h. The reaction mixture was partitioned between water and ethyl acetate (~4 mL total volume), and the aqueous phase was extracted with ethyl acetate (3×2.5 mL). The combined organic phases were extracted with brine (2×2 mL), then dried over sodium sulfate and filtered. Excess solvent was evaporated from the filtered organic phase to afford 5-bromo-3-(hydroxymethyl)-l- methylpyridin-2(lH)-one (17.7 mg, 0.073 mmol, 43.7% yield) as a clear, pale yellow oil. LCMS MH+: 217.9. HPLC Ret. Time 0.51 min. Method Bl . NMR (400 MHz, CHLOROFORM-d) delta 7.42 (s, 2H), 4.57 (d, J=6.2 Hz, 2H), 3.56 (s, 3H), 3.41 (t, J=6.4 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227502-35-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; HAQUE, Tasir Shamsul; WHITELEY, Brian K.; GILMORE, John L.; (192 pag.)WO2019/28302; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 79055-59-7 ,Some common heterocyclic compound, 79055-59-7, molecular formula is C6H7BrN2, 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.

EXAMPLE 51 4-Amino-N-(2-methyl-6-methylamino-pyridin-4-yl)-benzenesulfonamide 1.54 g (0.0082 mol) of 4-amino-2-bromo-6-methyl-pyridine were dissolved in 25 ml of pyridine, treated with 2.9 g (0.0124 mol) of 4-acetamino-benzenesulfochloride and stirred at 60 C. for 16 hours. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate as the eluent. The product-containing fractions were freed from solvent and dried in a high vacuum. There were obtained 2.17 g (69%) of N-[4-(2-bromo-6-methyl-pyridin-4-ylsulfamoyl)-phenyl]-acetamide as colourless crystals; m.p.: 262-264 C. (dec.).

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. 79055-59-7, 2-Bromo-6-methylpyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US5932599; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 72093-04-0 , The common heterocyclic compound, 72093-04-0, name is 3-Chloro-4-methylpyridine, molecular formula is C6H6ClN, 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.

General procedure: To a tube equipped with a magnetic stir bar were added the Pd catalyst 1 (12.6 mg, 0.45 mol% Pd) and 1.0 equiv. of heteroaryl chloride (0.2 mmol) in turn. Subsequently, the solvent (toluene, 2.0 mL) and phenylmagnesium bromide (0.3 mmol, 1.5 equiv) were added under N2 atmosphere, respectively. The reaction was then heated to 140 C and stirred until heteroaryl chloride was completely consumed as determined by TLC. At last, the reaction mixture was purified by silica gel column chromatography to afford the desired pure coupling product.

The synthetic route of 72093-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Xing; Zhu, Tingting; Shao, Zhongqi; Li, Yingjun; Chang, Honghong; Gao, Wenchao; Zhang, Yongli; Wei, Wenlong; Tetrahedron; vol. 72; 1; (2016); p. 69 – 75;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 130473-27-7, 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. 130473-27-7, name is 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, molecular formula is C8H6N2O2, 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 ethyl 1 H-pyrrolo [2,3-c] PYRIDINE-5-CARBOXYLATE [prepared according to M. Dekhane, P. Potier, R. H. Dodd, Tetrahedron, 1993,49, 8139-8146] (0.50 G, 2.63 MMOL) in DMF (10 mL) under a nitrogen atmosphere was added sodium hydride (0.087 g, 80% in mineral oil, 2.89 mmol) and 2, 4-difluorobenzyl bromide (0. 60g, 2.89 mmol). The resulting mixture was stirred for 16 hours at ambient temperature. It was quenched with water (30 ML}, and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were washed with water (2 x 30 mL), dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. Elution with hexane: ethyl acetate (1: 1) provided the title compound as a light yellow solid (0.40 g, 48% YIELD). 1 H NMR (CD3OD) #; 8.86 (s, 1 H), 8.47 (s, 1 H), 7.71 (d, 1 H, J = 3. 2Hz), 7.31 (dd, 1 H, J = 6. 3Hz), 6.94-7. 05 (m, 2H), 6.79 (d, 1 H, J = 3.2Hz), 5.63 (s, 2H), 4.46 (q, 2H, J = 7.3Hz), 1.45 (t, 3H, J = 7.3Hz). LCMS (API-ES, M+H+) : 317.0.

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 130473-27-7, 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid.

Reference:
Patent; PFIZER INC.; WO2004/39803; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 929617-30-1 ,Some common heterocyclic compound, 929617-30-1, molecular formula is C7H6BrN3, 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.

Example 325e 5-Bromo-1,3-dimethyl-1H-pyrazolo[3,4-c]pyridine 325e and 5-Bromo-2,3-dimethyl-2H-pyrazolo[3,4-c]pyridine 326a A mixture of 325d (3.0 g, 14.2 mmol), CH3I (2.40 g, 17.0 mmol), and K2CO3 (2.9 g, 21.3 mmol) in acetonitrile (60 mL) was stirred at 30C for 1 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 8:1 petroleum ether/ethyl acetate to afford 325e (920 mg, 29.0%) as a white solid, and eluting with 2:1 petroleum ether/ethyl acetate to afford 326a (390 mg, 12.0%) as a gray solid. MS-ESI: [M+H]+ 226.1.

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. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
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. 31181-88-1, name is 5-Fluoropicolinaldehyde. A new synthetic method of this compound is introduced below., SDS of cas: 31181-88-1

a) 2-Ethynyl-5-fluoro-pyridine To a mixture of 5-fluoro-2-formylpyridine (1.10 g, 9.0 mmol) in MeOH (38 mL) was added potassium carbonate (2.44 g, 0.018 mol) followed by a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (2.03 g, 11 mmol) in MeOH (12 mL). The mixture was stirred at room temperature for 90 min, then extracted with diethylether. The organic layers were then washed with sodium hydrogen carbonate solution (1 M) and brine, dried over sodium sulfate, filtered and evaporated at to give the title compound (1.01 g, 78%) as a light brown liquid. MS: m/e=121.0 [M]+.

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, 31181-88-1, 5-Fluoropicolinaldehyde.

Reference:
Patent; Hernandez, Maria-Clemencia; Lucas, Matthew C.; Thomas, Andrew; US2012/115844; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 145255-19-2, 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. 145255-19-2, name is 5-Aminopyridine-2-carboxamide, molecular formula is C6H7N3O, 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 2,4-dichloro-6-fluoro-benzoyl chloride (2.5 g, 11.0 mmol) and DIEA (4.8 mL, 27 mmol) in 1 -methyl -pyrrolidin-2 -one (25 mL) at 0 C was added a solution of 5-aminopyridine-2- carboxamide (1.51 g, 11.0 mmol) in dichloromethane (12.5 mL) dropwise. The reaction was allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was diluted with water (20 mL) and the resulting suspension was filtered to provide 5-[(2,4-dichloro-6-fluoro-benzoyl)amino]pyridine-2- carboxamide (1.2 g, 33%). ESI-MS m/z calc. 326.99, found 328.1 (M+l)+; retention time (Method B): 1.16 minutes (3 minute run). NMR (400 MHz, DMSO-d6) delta 11.34 (s, 1H), 8.88 – 8.82 (m, 1H), 8.29 (dd, J = 8.5, 2.5 Hz, 1H), 8.12 – 8.01 (m, 2H), 7.76 (dq, J = 4.2, 2.0 Hz, 2H), 7.58 (s, 1H) ppm.

According to the analysis of related databases, 145255-19-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem