Tag: M.W:100-200

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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C7H6F3NO

Step a: To a -78 C solution of diisopropylamine (0.966 mL, 6.77 mmol) in THF (20 mL) was added n-BuLi (1.6 M in hexanes, 4.23 mL, 6.77 mmol) dropwise and the reaction mixture was stirred for 5 mm at -78 C. A solution of 2-methoxy-3- (trifluoromethyl)pyridine (1.2 g, 6.77 mmol) in THF (10 mL) was added and the resulting mixture was stirred for 2 h at -78 C. ?2 (1.72 g, 6.77 mmol) in THF (5 mL) was added at -78 C and the resulting mixture was allowed to warm to RT within 30 mm and was further stirred at this temperature for 30 mm. The volatiles were removed under reduced pressure, the residue was dissolved in Et20 (200 mL) The organic layer was washed sequentially with sat. aq. Na25203 (200 mL), sat. aq. NH4C1 (200 mL), and sat. aq. NaHCO3 (200 mL), dried over Mg504, filtered, and the volatiles were removed under reduced pressure. The residue was purified by silica chromatography (0 to 25% gradient of EtOAc/heptane) to give 4-iodo-2-methoxy-3- (trifluoromethyl)pyridine (540 mg, 1.354 mmol). MS m/z 304.0 (M+H).

The synthetic route of 121643-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEN, Zhuoliang; FORTANET, Jorge Farcia; LAMARCHE, Matthew J.; SENDZIK, Martin; TAMEZ, JR., Victoriano; YU, Bing; (237 pag.)WO2016/203405; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 850663-54-6, 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. 850663-54-6, name is 4-Chloro-5-nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

A suspension of 2-hydroxy-4-chloro-5-nitropyridine (86.2 mmol, 15 g) in phosphorus oxychloride (50 mL) was heated at 80C for 3.5 hours. The excess phosphorus oxychloride was removed under reduced pressure and the residue partitioned between dichloromethane and 10% aqueous sodium carbonate solution. The aqueous phase was further extracted with dichloromethane (3 x 100 mL) . The combined organic extracts were dried (MgS04) then concentrated under reduced presssure to give the title compound as dark oil which solidified on standing (7.19 g, 43%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60753-14-2, 4-(Pyridin-3-yl)butan-1-ol, 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, HPLC of Formula: C9H13NO, blongs to pyridine-derivatives compound. HPLC of Formula: C9H13NO

Step A 4-pyridin-3-yl-butyraldehyde To a solution of oxalyl chloride (0.74 mL in 5 mL dry methylene chloride) at -78 C. was added a solution of methyl sulfoxide (0.90 mL in 5 mL methylene chloride) and the mixture stirred at low temperature for 15 minutes. A solution of 4-pyridin-3-yl-butan-1-ol (prepared essentially as described in Example 2.1, 820 mg in 10 mL methylene chloride) and the reaction allowed to proceed for 45 minutes after which time 4 mL triethylamine were added and the mixture allowed to warm to room temperature. After 35 minutes saturated sodium bicarbonate was addded and the mixture extracted with methylene chloride. The organic portion was washed with saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo to give the crude title compound (813 mg).

The synthetic route of 60753-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5849764; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55052-27-2, 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. 55052-27-2, name is 6-Chloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5ClN2, 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.

The title compound of Preparation 57 (1.00 g, 6.55 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (1.0 ml, 7.2 mmol) and potassium carbonate (2.72 g, 19.7 mmol) were suspended in 13 ml dimethoxyethane in a microwave reactor and submitted to three vacuum-argon cycles. [1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (0.29 g, 0.33 mmol) was added and the resulting mixture was submitted to three further vacuum-argon cycles. The mixture was stirred at 120ºC for 2h under microwave irradiation. The mixture was allowed to cool and was filtered through Celite, eluting with ethyl acetate. The filtrate was evaporated under reduced pressure and the residue was purified using the Isolera Purification System (ethyl acetate-hexane gradient, 0:100 rising to 50:50) to give 0.57 g (4.31 mmol, 65%) of the title compound as a beige solid. Purity 98%. [0443] 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 10.87 (br. s., 1 H), 7.86 (d, J=7.63 Hz, 1 H), 7.29 (dd, J=3.52, 2.35 Hz, 1 H), 6.97 (d, J=7.63 Hz, 1 H), 6.47 (dd, J=3.52,1.76 Hz, 1 H), 2.69 (s, 3 H). [0444] HPLC/MS (15 min) retention time 2.57 min. [0445] LRMS:m/z133(M+1).

According to the analysis of related databases, 55052-27-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Alonso Diez, Juan Antonio; Buil Albero, Maria Antonia; Eastwood, Paul Robert; Esteve Trias, Cristina; Lozoya Toribio, Maria Estrella; Roberts, Richard Spurring; Vidal Gispert, Laura; EP2548876; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1137-67-3 ,Some common heterocyclic compound, 1137-67-3, molecular formula is C12H9N3, 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: 2-Substituted benzimidazole (0.01 M) was added to the ethanolic solution of benzamide (0.01M). Formaldehyde (37-41% w/v) (0.01 M) was added and the reaction mixture was then adjusted to the pH of 3.5 with concentrated HCl. The mixture was kept at efficient ice cooling for half an hour. Then, it was refluxed with stirring at 80 C for 10-12h. Formaldehyde (37-41% w/v) was added to the reaction mixture in portions for completion of the reaction. End of reaction was monitored by TLC. Reaction mixture was kept in refrigerator overnight. Solvent was evaporated under reduced pressure and product was collected, washed with water and recrystallized from ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1137-67-3, its application will become more common.

Reference:
Article; Sethi, Ritchu; Arora, Sandeep; Saini, Deepika; Singh, Thakur Gurjeet; Jain, Sandeep; Acta poloniae pharmaceutica; vol. 74; 5; (2017); p. 1413 – 1425;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19842-08-1, 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 19842-08-1 as follows.

In a 2 L round-bottomed flask was charged n-butyllithium 2.5M hexanes (99 ml, 248 mmol) in Et2O (1680 ml) to give a colorless solution. The reaction was cooled to -78 C. n-Butyllithium 2.5M hexanes (99 ml, 248 mmol) was added dropwise keeping the temperature below -70 C. The reaction was stirred for 1 hour and N,N-dimethylformamide (36.6 ml, 473 mmol) was added keeping the temperature below -70 C. The reaction was stirred for 1 hour and quenched with saturated ammonium chloride solution (2 L). The organic layer was washed with brine, dried over sodium sulfate and solvent removed under reduced pressure. The crude residue was purified by column chromatography eluting with 0-30% ethyl acetate to give 6-bromonicotinaldehyde. Yield 19.7 g, 44.8%In a 2 L round-bottomed flask was added Methyltriphenylphosphonium bromide (42.9 g, 120 mmol) in THF (600 ml) and cooled to -20 C. n-Butyllithium 2.5M hexanes (48.0 ml, 120 mmol) was added dropwise keeping the temperature below 0 C. The reaction was warmed to room temperature for 20 minutes and cooled back to 0 C. A solution of 6-bromonicotinaldehyde (18.6 g, 100 mmol) in THF (40 mL) was added. The reaction was warmed to room temperature and stirred overnight. The reaction was partitioned between water and diethyl ether (1 L) and the organic layer was dried over sodium sulfate, filtered and solvent removed at room temperature under reduced pressure. The product, 2-bromo-5-vinylpyridine, was purified by bulb to bulb distillation (600 mTorr, 80-100 C.). Yield 17.2 g, 93%2-Bromo-5-vinylpyridine (17.2 g, 40.1 mmol) was dissolved in ethanol (150 mL) and Adam’s Catalyst (PtO2, 75%, 1.4 g) was added. The mixture was hydrogenated at 3 psi of hydrogen, continually checking the progress of the reaction by LC and 1H NMR between each charge of hydrogen. After 10 psi was consumed, the data showed completion of the reaction with <5% of reduction of the bromine. The catalyst was filtered off and the solvent was removed under reduced pressure at 20 C. to give 2-bromo-5-ethylpyridine. Yield 17 g, 98%.In a 1 L round-bottomed flask was compound 6 (10 g, 53.8 mmol) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (13.83 g, 59.1 mmol) in Dioxane (300 ml) followed by saturated sodium bicarbonate (150 ml). The mixture was degassed by passing a stream of nitrogen through the mixture for 20 minutes. Tetrakis(triphenylphosphine) palladium(0) (3.36 g, 2.91 mmol) was added and the mixture was heated to reflux becoming very thick then finally going to solution. The reaction was heated for 2 hours, cooled to room temperature and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure. The residue was purified by column chromatography 0-100% ethyl acetate/heptane to give 3-(5-ethylpyridin-2-yl)-4-methylaniline. Yield 8.7 g, 77%The urea was formed from 3-(5-ethylpyridin-2-yl)-4-methylaniline and 4-(2-amino-5-tert-butylthiophene-3-carbonyl)-3,3-dimethylpiperazine-2-one. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19842-08-1, its application will become more common. Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); A1;,
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. 131747-53-0, name is (6-(Trifluoromethyl)pyridin-2-yl)methanol, the common compound, a new synthetic route is introduced below. Recommanded Product: (6-(Trifluoromethyl)pyridin-2-yl)methanol

Step 3; (6-Trifluoromethylpyridin-2-yl)methanol (760 mg, 4.3 mmol) was dissolved in CH2Cl2 and thionyl chloride was added slowly at room temperature. The reaction mixture was stirred at room temperature for 4 h. Solvent was removed under the reduced pressure, the pH was adjusted to 5, and the product was extracted with EtOAc. Purification by flash column ( 5% EtOAc-Hexane) gave 2-chloromethyl-6-trifluoromethylpyridine (200 mg) as a white solid.

The synthetic route of 131747-53-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; WO2006/34004; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1095823-39-4, Adding some certain compound to certain chemical reactions, such as: 1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine,molecular formula is C6H4ClF3N2, 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 1095823-39-4.

Synthesis of Compound S.7. To a solution of S.6 (205 mg, 0.64 mmol) in methylene chloride (4 mL) at rt was added oxalyl chloride (160 muL, 0.0019 mol) followed by the addition of DMF (50 muL) and stirred at RT for 1 hr. Separately a solution of A.6 (132 mg, 0.000672 mol), acetonitrile (2 ml) and pyridine (520 muL, 0.0065 mol) was stirred at RT followed by the addition of chlorotrimethylsilane (100 muL, 0.0008 mol). The acid chloride was concentrated under reduced pressure to a tan solid and redissolved in acetonitrile (2 mL). To the acid chloride solution was added the activated aniline. After 3 hr, the reaction mixture was diluted with ethyl acetate (75 mL) and washed with dilute citric acid (50 mL), aqueous sodium bicarbonate (50 mL) and water. The organic layer was dried over sodium sulfate and concentrated to a residue which was purified by to give compound S.7. MS m/z: 498.95 [M+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. 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.1074-98-2, name is 3-Methyl-4-nitropyridine 1-oxide, molecular formula is C6H6N2O3, molecular weight is 154.13, as common compound, the synthetic route is as follows.HPLC of Formula: C6H6N2O3

[0334] 3-Methyl-4-nitropyridine 1-oxide (24.1a, 12.0 g, 0.07786 mol) was dissolved in acetyl chloride (60.00 mL). The reaction was heated to reflux for 2 hours. After cooling the reaction was poured onto ice and was basified with anhydrous sodium carbonate and extracted with chloroform. The extract was dried with potassium carbonate and filtered. The chloroform was evaporated off to yield the desired product in high purity. (85% yield) The MP was taken and found to be at 124 C, which matches literature references.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1074-98-2, 3-Methyl-4-nitropyridine 1-oxide, and friends who are interested can also refer to it.

Reference:
Patent; ADOLOR CORPORATION; WO2008/63625; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 182181-42-6, 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine, 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, 182181-42-6, blongs to pyridine-derivatives compound. SDS of cas: 182181-42-6

67(D) 8-Methyi-2-(4-(trimethyisiiyi)but-3-ynyl)-imidazo[1,2-a]pvridine ;To a solution of trimethyl(prop-1-ynyl)silane (259 mg, 2.31 mmol) in THF (7.5 mL) at -78C was added n-BuLi 2.5M in hexane (1.1 mL, 2.8 mmol). After 90min at -78C 2-(chloromethyl)-8-methyl-imidazo[1,2-a]pyridine (500 mg, 2.8 mmol) in THF (5 mL) was added dropwise. The solution became blue-green at-78C. The solution was stirred at-78C for an additional 1h. The reaction was quenched with water and the solvent was removed under reduced pressure. The crude product was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH from 100/0 to 99/1 as eluent) to afford 590 mg of 8-methyl-2-(4-(trimethylsilyl)but-3-ynyl)- imidazo[1,2-a]pyridine (Yield : 100%) as an yellow oil. LCMS (RT) : 0.59-2.61min; MS (ES+) gave m/z : 257.1 Rf (DCM/MeOH : 95/5) : 0.22

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,182181-42-6, its application will become more common.

Reference:
Patent; ADDEX PHARMACEUTICALS SA; WO2005/123703; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem