Tag: M.W:100-200

1990-90-5, 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. 1990-90-5, name is 3-Methylpyridin-4-amine, molecular formula is C6H8N2, 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.

Step 1: tert-butyl (3-methylpyridin-4-yl)carbamate (6B) To a solution of 3-methylpyridin-4-amine (6A) (38.0 g, 0.35 mol) in 1-butanol (300 mL) was added (Boc)2O (84.3 g, 0.38 mol). The mixture solution was stirred at r.t. for 8 hours. Then the solution mixture was diluted with EA (1000 mL), washed with water (2*500 mL) and brine (1*250 mL), dried with Na2SO4 and concentrated. The crude product was purified by flash chromatography to afford the title compound 6B (73.0 g, 99%) as a white solid.

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. 1990-90-5, 3-Methylpyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fronthera U.S. Pharmaceuticals LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; LI, Yao; (169 pag.)US2019/367515; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. 117519-09-2

Example 117 [5-TRIFLUOROMETHYL-2- [4- (3-TRIFLUOROMETHYL-PYRIDIN-2-YL)-PIPERAZIN-1-YL]-LH-] imidazo [4,5-b] pyridine, trifluoroacetic acid salt. (a) [N2-(4-METHOXY-BENZYL)-6-TRIFLUOROMETHYL-PYNDINE-2,] 3-diamine. A mixture of the [3-AMINO-2-CHLORO-6- (TRIFLUOROMETHYL)] pyridine (416 mg, 2.1 mmol, Matrix), 4-methoxy-benzylamine (294 mg, 2.1 mmol, Aldrich) and sodium bicarbonate (265 mg, 3.2 mmol) in isoamyl alcohol (0.6 mL) was heated at [220 C] in a microwave synthesizer for 30 min. The reaction mixture was then cooled to room temperature, diluted with MeOH (5 mL), filtered and the filtrate was evaporated in vacuo. The residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound as a yellow oil. MS (ESI, pos. ion) [M/Z] : 298 [(M+1)]

Statistics shows that 117519-09-2 is playing an increasingly important role. we look forward to future research findings about 3-Amino-2-chloro-6-(trifluoromethyl)pyridine.

Reference:
Patent; AMGEN INC.; WO2004/35549; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

620-08-6, Adding a certain compound to certain chemical reactions, such as: 620-08-6, 4-Methoxypyridine, 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, 620-08-6, blongs to pyridine-derivatives compound.

4-methoxypyridine 2a (0.5 mmol) and aniline 3a (0.75 mmol) were sequentially added to the reaction tube under N2 atmosphere.a mixture obtained by dissolving a base (0.75 mmol) of THF and a solvent (0.5 ml) in a concentration of 1.0 M in advance,Heat to T C, stir the reaction for about 16 h until the conversion of the raw materials is completed, and return to room temperature.Diluted with THF (3 ml) to the reaction mixture.Filtered on silica gel or diatomaceous earth, washed with THF,The crude product was concentrated in vacuo and subjected to silica gel column chromatography to give the corresponding product 1aa.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,620-08-6, its application will become more common.

Reference:
Patent; Hunan University; Wang Xueqiang; Tan Weihong; Wang Xia; Long Chengyu; Huang Sijie; (22 pag.)CN109608394; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 109-04-6, 2-Bromopyridine, 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, 109-04-6, blongs to pyridine-derivatives compound. 109-04-6

Example 32; 2-tributylstannylpyridine (18); Butyllithium (2.5 M in hexane, 6.33 mmol) is added to a solution of 2-bromopyridine (1 g, 6.33 mmol) in THF (12 mL) freshly distilled and degassed at -78 C. The reddish solution is stirred for 30 minutes at -78 C. Tributyltin chloride (1.7 mL, 6.33 mmol) is then added and the solution is stirred for 1 hour -78 C. and for 1 hour at room temperature. The mixture is treated with a NH4Cl saturated solution and extracted with diethylic ether. The organic phase is washed with a NaCl saturated solution, dried over MgSO4 and concentrated under reduced pressure. The residue is submitted to aluminium column chromatography (hexane/AcOET: 20/1), thus providing a pure product with a yield of 94%.1H RMN (CDCl3) delta (ppm): 8.73 (ddd, J=4.9, 1.9, 1.0, 1H, H6), 7.48 (dt, J=7.4, 1.8, 1H, H5), 7.39 (dt, J=7.4, 1.6, 1H, H3), 7.10 (ddd, J=6.9, 4.9, 1.7, 1H, H4), 1.70-1.05 (m, 18H, CH2), 0.85 (t, 9H, J=7.3, CH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109-04-6, its application will become more common.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.; US2010/4443; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

16063-70-0, Adding a certain compound to certain chemical reactions, such as: 16063-70-0, 2,3,5-Trichloropyridine, 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, 16063-70-0, blongs to pyridine-derivatives compound.

40.0 g of 2,3,5-trichloropyridine was dissolved in 240 g of dimethyl sulfoxide.65.2 g of methyl cyanoacetate and 75.8 g of potassium carbonate were sequentially added to the reaction solution.The reaction was stirred at 120 C. for 7.5 hours.After completion of the reaction, the reaction solution was cooled to 40 C., and 200 g of water and 114 g of 35 mass% hydrochloric acid were added to the reaction solution.The reaction was stirred at room temperature for 1 hour.The solid precipitated in the reaction solution was separated by filtration.The obtained solid was washed sequentially with 50 g of water, 50 g of normal hexane, and 100 g of diisopropyl ether, and then dried under reduced pressure to obtain 41.8 g of the desired product as a yellow solid (yield: 77.7%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16063-70-0, its application will become more common.

Reference:
Patent; Nissan Chemical Industries, Ltd.; Nakayama, Yosuke; Saito, Fumiyo; Nanju, Yusuke; (53 pag.)JP2019/34892; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1122-54-9, name is 4-Acetylpyridine. This compound has unique chemical properties. The synthetic route is as follows. 1122-54-9

[00234] To a solution of l-(pyridin-4-yl)ethanone (1.0 g, 8.25 mmol) in HOAc (60 mL) under ice bath was added aqueous HBr (1 mL, 48%) and Br2 (1.45 g, 9.1 mmol) in HOAc (20 mL). The mixture was stirred at rt for 4 h during which time a precipitate formed. Filtration of the solid provided 2-bromo-l-(pyridin-4-yl)ethanone hydrobromide (0.72 g, 3.6 mmol) as a yellow solid. LC/MS [M+H]+ = 200.1.

Statistics shows that 1122-54-9 is playing an increasingly important role. we look forward to future research findings about 4-Acetylpyridine.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; NEWCOM, Jason, S.; SPEAR, Kerry, L.; WO2015/88564; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

17368-12-6, 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. 17368-12-6, name is 2-Chloro-4-hydroxypyridine. A new synthetic method of this compound is introduced below.

A mixture of 5-fluoro-4-methyl-2-nitropyridine (2 g, 12.81 mmol) and 2-chloro-4-hydroxypyridine (1.66 g, 12.81 mmol) in DMF (26 mL) was sparged with Ar, treated with K2CO3 (2.66 g, 19.22 mmol), heated at 88 C. for 24 h, then at 50 C. for 2 days. The mixture was treated with water and the resulting solid collected via filtration and dried to afford 5-((2-chloropyridin-4-yl)oxy)-4-methyl-2-nitropyridine (2.72 g, 80%). 1H NMR (400 MHz, DMSO-d6): delta 8.49 (s, 1H), 8.47 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 7.24 (d, J=2.3 Hz, 1H), 7.12 (dd, J=5.7, 2.3 Hz, 1H), 2.32 (s, 3H); MS (ESI) m/z: 266.0 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17368-12-6, 2-Chloro-4-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding some certain compound to certain chemical reactions, such as: 393-53-3, name is 3-Fluoroisonicotinic acid, 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 393-53-3. 393-53-3

General Procedure: To a 50 mL round bottom flask equipped with a stir bar and a reflux condenser were added 3-fluoroisonicotinic acid (1.0 g, 7.09 mmol), methanol (10 mL) and sulfuric acid (4.2 mL). The reaction mixture was heated at 70 C overnight, cooled to room temperature and concentrated in vacuo. The residue was cooled in an ice bath, basified to pH 9 using saturated aqueous sodium carbonate and extracted with ethyl acetate (2x). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the desired product as yellow oil (1.03 g, 94 %). 1H NMR (300 MHz, CDCl3): delta 8.62 (d, IH), 8.54 (d, IH), 7.77 (t, IH), 3.98 (s, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 393-53-3.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2007/87135; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

74115-13-2, 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.74115-13-2, name is 5-Bromo-3-pyridinol, molecular formula is C5H4BrNO, molecular weight is 174, as common compound, the synthetic route is as follows.

General procedure for Mitsunobu Reaction (Method A). To a mixture of 5-Bromo-3- pyridinol (1.2 equiv) and Ph3P (1.6 equiv) in anhydrous THF taken in a flame-dried flask under N2, N-Boc protected alcohol (1 equiv) was added and the mixture was cooled to – 10 C. Diethyl azodicarboxylate (40% w/v) in toluene (1.6 equiv) was added dropwise to the mixture and was warmed gradually to the room temperature. After 48 h, the reaction mixture was quenched with 1 mL of water and the solvent was removed under reduced pressure. The resulting yellow oil was purified by column chromatography on silica gel to yield 55-60% as a white solid. Example 3(S)-tei”i-butyl-2-((5-bromopyridin-3-yloxy)methyl)azetidine-l-carboxylate (VMY-2-3): Method A was used. Yield 55% (white solid). 1H NMR (400 MHz, CDC13) ? 8.25 – 8.19 (m, 2H), 7.36 (s, 1H), 4.44 (d, J= 5.3, 1H), 4.32 – 4.20 (m, 1H), 4.06 (dd, J = 2.8, 10.1, 1H), 3.81 (t, J= 7.5, 2H), 2.36 – 2.14 (m, 2H), 1.36 (s, 9H). 13C NMR (100 MHz, CDC13 ) ? 156.07,155.41, 143.13, 136.65, 124.02, 120.28, 79.76, 69.00, 59.92,47.14, 28.37, 18.95.HRMS (ESI): exact mass calcd for Ci4Hi9BrN203 [M+H]+, 343.0657, found 343.0670.

Statistics shows that 74115-13-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-pyridinol.

Reference:
Patent; GEORGETOWN UNIVERSITY; DUKE UNIVERSITY; BROWN, Milton, L.; PAIGE, Mikell, A.; XIAO, Yingxian; KELLAR, Kenneth, J.; YENUGONDA, Venkata, Mahidhar; LEVIN, Edward, D.; REZVANI, Amir, H.; WO2013/71067; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1990-90-5, 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. 1990-90-5, name is 3-Methylpyridin-4-amine, molecular formula is C6H8N2, 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 intermediate 23d (100 mg) in CH2Cl2 (7 mL) were at 0 C. consecutively added N,N-diisopropyl ethylamine (140 muL), 3-methylpyridin-4-amine (40 mg) and bromotripyrrolidino phosphonium hexafluorophosphate (230 mg) and the resulting mixture was stirred at ambient temperature for 2 h. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (Interchim cartridge 15SiHP/25 g, Cy/EtOAc) to yield the desired compound (84% yield). [0490] LC-MS (Method 2): m/z [M+H]+=341.1 (MW calc.=340.81); Rt=0.57 min.

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. 1990-90-5, 3-Methylpyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem