Tag: M.W:200-300

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

Application of 109306-86-7 ,Some common heterocyclic compound, 109306-86-7, molecular formula is C11H8BrN, 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.

(a) 2-[2-(2-Pyridyl)-phenyl thio]-benzoxazole 2-Mercapto benzoxazole (604 mg; 4 mmole) was reacted with 2-(2-bromophenyl)pyridine (936 mg; 4 mmole) in the presence of KOH (224 mg; 4 mmole) in N-methyl pyrrolidine (16 ml). The mixture was heated under reflux for 6 hours, worked up and flash chromatographed (silica), using ethyl acetate/petroleum ether (2/3) eluant to give the sub-title compound as a pale brown oil (52 mg; 4.3%). m/z 304, 281, 277, 271, 186 (Base Peak), 154, 135.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109306-86-7, its application will become more common.

Reference:
Patent; Fisons plc; US4900751; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75073-11-9, 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.75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine, molecular formula is C6H7IN2, molecular weight is 234.04, as common compound, the synthetic route is as follows.

(B) 6-iodo-5-methylimidazo[1,2-a]pyridine (0308) To a solution of 5-iodo-6-methylpyridin-2-amine (7.5 g, 32 mmol) in ethanol (400 mL) was added 2-chloroacetaldehyde aqueous solution (18 mL, 40%), and the mixture was stirred at 80 C for 16 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with water, neutralized with 30% aqueous sodium hydroxide solution, and extracted with dichloromethane (150 mL×3). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (6.0 g). MS: [M+H]+ 259.1

Statistics shows that 75073-11-9 is playing an increasingly important role. we look forward to future research findings about 5-Iodo-6-methylpyridin-2-amine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, 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, Computed Properties of C13H17NO4, blongs to pyridine-derivatives compound. Computed Properties of C13H17NO4

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
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. 936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride, the common compound, a new synthetic route is introduced below. Recommanded Product: 5-Bromo-2-(chloromethyl)pyridine hydrochloride

To an N,N-dimethylformamide (40.0 mL) solution of 4-fluorophenol (3.00 g, 26.8 mmol) was added sodium hydride (1.00 g, 25.0 mmol, 60percent in oil) on an ice bath (0° C.) under nitrogen atmosphere, which was stirred for 20 minutes at room temperature. To the reaction solution was then added a mixture of 5-bromo-2-chloromethyl-pyridine hydrochloride (4.6 g, 22.3 mmol) described in Manufacturing Example 54-1-2 and triethylamine (30.6 mL, 20.4 mmol), which was stirred for 10 minutes at room temperature. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. This organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated from the filtrate under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate_heptane=1:4) to obtain the title compound (4.0 g, 63.6percent). 1H-NMR Spectrum (CDCl3) delta (ppm): 5.10 (2H, s), 6.88-6.91 (2H, m), 6.95-6.99 (2H, m), 7.40-7.42 (1H, m), 7.81-7.84 (1H, m), 8.64-8.65 (1H, m).

The synthetic route of 936342-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 112006-57-2, 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 112006-57-2, name is 2-(Benzylthio)-N,N-dimethylnicotinamide. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 N,N-Dimethyl-2-aminosulfonyl-3-pyridinecarboxamide A mixture of 4.4 ml of concentrated hydrochloric acid, 66 ml of methylene chloride, 34 ml of water and 4.0 g (14.7 mmol) of the N,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide was cooled to 0 C. Maintaining a temperature of -5 to 3 C., 60 ml (40.5 mmol) of 5% sodium hypochlorite was added dropwise over 15 minutes. The resulting yellow emulsion was stirred at 0 C. an additional 20 minutes. The reaction mixture was then poured into water and extracted with methylene chloride. The combined organic extracts were kept at 0 C. and washed with a saturated sodium bisulfite solution and dried over sodium sulfate. After 30 minutes, the yellow solution was filtered into a reaction flask and cooled to -78 C. and 5 ml (431 mmol) of dry ammonia added. The reaction mixture was allowed to warm to room temperature and the solvent removed under reduced pressure. The resulting solid was slurried with 5 ml of water and the insoluble white solid collected by filtration to provide 2.0 g of the subject compound, m.p. 198-209 C.(d). NMR (DMSO): delta 2.70 (s, 3H, NCH3); 2.93 (s, 3H, NCH3); 7.60-7.75 (m, 1H); 7.90 (m, 1H); and 8.75 (m, 1H).

According to the analysis of related databases, 112006-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4789393; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 77199-09-8, 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 77199-09-8, name is Ethyl 5-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 256 Production of ethyl 5-ethenylpyridine-2-carboxylate A mixture of the compound of Reference Example 255 (20.0 g, 86.9 mmol), tributylvinyltin (28.1 mL, 95.6 mmol), Pd(PPh3)4 (2.01 g, 1.74 mmol) and DMF (100 mL) was stirred at 100C for 2 hr under an argon atmosphere. To the reaction mixture was added water (200 mL), and the mixture was extracted with ethyl acetate (400 mL). The extract was washed with brine (200 mL), and dried over anhydrous sodium sulfate. The insoluble material was removed by filtration, and the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=98:2?20:80) to give the title compound (16.5 g, 100%) as a pale-yellow oil. 1H NMR (300 MHz, DMSO-d6) delta:1.33 (3 H, t, J = 7.1 Hz), 4.34 (2 H, q, J = 7.1 Hz), 5.56 (1 H, d, J = 11.1 Hz), 6.14 (1 H, d, J = 17.8 Hz), 6.87 (1 H, dd, J = 11.1, 17.8 Hz), 8.00-8.06 (1 H, m), 8.07-8.16 (1 H, m), 8.80 (1 H, d, J = 1.9 Hz).

According to the analysis of related databases, 77199-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2471789; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886373-28-0, Adding some certain compound to certain chemical reactions, such as: 886373-28-0, name is 5-Bromo-3-fluoropicolinonitrile,molecular formula is C6H2BrFN2, 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 886373-28-0.

Cone. HCl (300 mL) were added to 5-Bromo-3-fluoro-pyridine-2-carbonitrile (21.0 g,0.11 mol) and stirred over night at 600C. After evaporation ether was added and the suspension was stirred for additional time. The solid was collected and dried. The crude product was used without any further purification. MS (m/z): 219.8 [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. 886373-28-0, 5-Bromo-3-fluoropicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JERINI AG; WO2009/36996; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 77199-09-8, name is Ethyl 5-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 77199-09-8

2-Amino-5-fluoro-4-(l-isopropyl-2-methyl-lH-imidazol-5-yl)pyrimidine (Method 1 ; 517mg, 2.2mmol), ethyl 5-bromopyridine-2-carboxylate (460.12mg, 2mmol), EPO tris(dibenzylideneacetone)dipalladium(0) (18.31mg, lmol%), Xantphos (25.5mg, 2.2mol%) and caesium carbonate (912.3mg, 2.8mmol) in anhydrous 1,4-dioxane (8ml) were evacuated and refilled with nitrogen (3 times). The reaction was heated under nitrogen at 100C for 3.5h. Extra tris(dibenzylideneacetone)dipalladium(0) (18.31mg, lmol%) and Xantphos (25.5mg, 2.2mol%) were added and the reaction mixture was heated under nitrogen at 1000C overnight before evaporating under reduced pressure. The residue obtained was partitioned between DCM and water and the aqueous layer was extracted with DCM twice. The organics were combined, washed with brine, dried and the solvent was evaporated to give a foam which was purified by reverse phase chromatography (acidic prep HPLC system). The product containing fractions were passed through a pre-equilibrated Isolute SCX-2 column, eluted with MeOH, and a 7 molar solution of ammonia in MeOH. Evaporation of solvent gave the title compound as a solid which was dried in vac oven overnight at 5O0C (540mg, 70%). NMR (400MHz): 1.33 (t, 3H), 1.48 (d, 6H), 2.54 (s, 3H), 4.32 (q, 2H), 5.39 (septet, IH), 7.41 (d, IH), 8.02 (d, IH), 8.35 (dd, IH), 8.67 (d, IH), 8.91 (d, IH), 10.16 (s, IH); 17F NMR (400MHz): -145.98 (t, IF); m/z 385.

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, 77199-09-8, Ethyl 5-bromopicolinate.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/95159; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 185017-72-5, 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.185017-72-5, name is 3-Bromo-2-chloro-6-picoline, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.

Example 52; (RS)-1-Benzenesulfonyl-4-[4-(3-bromo-6-methyl-pyridin-2-yl)-piperazine-1-carbonyl]-3-cyclohexyl-imidazolidin-2-oneStep 1: A solution of 3-bromo-2-chloro-6-picoline (0.2 g), piperazine (0.083 g) and triethylamine (0.096 g) in acetonitrile (5 ml) was heated in the microwave apparatus: 30 min at 120 C. followed by 60 min at 150 C. and 30 min at 170 C. The mixture was concentrated and the product was purified by chromatography (SiO2, CH2Cl2=>CH2Cl2/CH3OH 4:1) to give 1-(3-bromo-6-methyl-pyridin-2-yl)-piperazine (0.05 g) as a light yellow solid.

Statistics shows that 185017-72-5 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; Dehmlow, Henrietta; Kuhn, Bernd; Sander, Ulrike Obst; Roever, Stephan; Schulz-Gasch, Tanja; Wright, Matthew; US2008/242677; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem