Tag: M.W:100-200

Reference of 121643-44-5, 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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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.

2-Methoxy-3-trifluoromethyl-pyridine (2.7 g, 14.79 mmol) and 1 ,3-dibromo-5,5- dimethylhydantoin (5.28g, 18.48 mmol) were placed in a round-bottom flask. To this mixture was slowly added 40ml TFA. The mixture was stirred overnight at ambient temperature (16h). After completion of the reaction, TFA solvent was evaporated in vacuo and the resulting residue was neutralized to pH6-7 by the addition of saturated NaHC03. The aqueous layer was extracted with DCM two times and the combined extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give a mixture of oil and white solid. The residue was redissolved into 20% Ethylacetate/Heptane (50ml) and the insoluble white solid was filtered off. The filtrate was concentrated and then purified by Flash- chromatography on silica gel (EtOAc/Heptane 5/95) to give 5-Bromo-2-methoxy-3- trifluoromethyl-pyridine as a colorless liquid (2.08 g, 52% yield).1 H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

According to the analysis of related databases, 121643-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; LEWIS, Ian; SMITH, Alexander, Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; WOLF, Romain; ZECRI, Frederic; WO2013/57711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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. HPLC of Formula: C6H6ClNO

A suspension of 2-(5-chloro-2,4-dimethoxyphenyl)-7-(piperazin-l-yl)imidazo[l,2- a]pyridine 1 (100 mg, 0,27 mmol), 2-chloro-5-methoxypyridine (42 mg, 0.29 mmol), (±)BINAP (17 mg, 0.027 mmol) and t-BuOK (90 mg, 0.80 mmol) in 1 ,4-dioxane (20 mL) was degassed with argon for 15 min. The mixture was then charged with Pd(OAc)2 (9.0 mg, 0.013 mmol) and degassed with argon for another 5 min. The resulting reaction mixture was stirred at 100- 1 10 C for 16 h in a sealed tube. The reaction mixture was cooled, filtered through a pad of celite and evaporated to dryness. The residue obtained was purified by combi-flash companion (silica gel, CH3OH/CH2Cl2) to provide 2-(5-chloro-2,4-dimethoxyphenyl)-7-(4-(5-methoxypyridin-2-yl)piperazin-1-yl)imidazo[1,2-a]pyridine 303b (25 mg, 19%) as an off-white solid. 1H NMR (400 MHz, DMSO-t/,.). delta 8.33 id. 2.8 Hz, 1H), 8.35 (d, J =7.6 Hz, 1H), 8.18 (s, 1H), 8.03 (m, I I I ). 7.91 (d, J= 2.8 Hz, i l l). 7.30 (dd, J =9.2, 3.2 Hz, IH), 6.91 (d. ./ 9.2 Hz, IH), 6.87 (s, IH), 6.85 (d, ./ 2.4 Hz, IH), 6.27 (s, IH), 4.01 (s, 3H), 3.93 (s, 3H), 3.74 (s, 3H), 3.54-3.52 (m, 4H), 3.51 -3.32 (m, 4H); HPLC (Method 1) 92.8% (AUC), = 1 1.80 min,; ESI+APC1 MS m/z 480 [M + H]+

With the rapid development of chemical substances, we look forward to future research findings about 139585-48-1.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72617-82-4, 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.72617-82-4, name is 6-(2,2,2-Trifluoroethoxy)pyridin-3-amine, molecular formula is C7H7F3N2O, molecular weight is 192.14, as common compound, the synthetic route is as follows.

Step 3: 8-Hydroxy-2-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-2-aza-spiro[4.5]decan-1-one 6-(2,2,2-Trifluoro-ethoxy)-pyridin-3-ylamine (5.11 g, obtained in example 108, step 2) was added to a solution of 4-hydroxy-1-(2-methoxy-ethyl)-cyclohexanecarboxylic acid ethyl ester (5.10 g, obtained in example 2, step 3) in toluene (160 mL).

Statistics shows that 72617-82-4 is playing an increasingly important role. we look forward to future research findings about 6-(2,2,2-Trifluoroethoxy)pyridin-3-amine.

Reference:
Patent; Ackermann, Jean; Brugger, Stephan; Conte, Aurelia; Hunziker, Daniel; Neidhart, Werner; Nettekoven, Matthias; Schulz-Gasch, Tanja; Wertheimer, Stanley; US2011/92512; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 102645-33-0, name is 2,5-Dichloroisonicotinaldehyde, molecular formula is C6H3Cl2NO, 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. name: 2,5-Dichloroisonicotinaldehyde

Intermediate 9: (2. 5-Dichloro-4-pyridinvl) methanedivl diacetate; Concentrated sulfuric acid (3 drops) was added to a suspension of 2, 5-dichloro-4- pyridinecarbaldehyde (Intermediate 8,4. 0g) in acetic anhydride (25ml) and the mixture was stirred at room temperature for 20h. The acetic anhydride was removed under vacuum to give the title compound as a pale brown oil. LC-MS: Rt 2.94min, MH+ 278

With the rapid development of chemical substances, we look forward to future research findings about 102645-33-0.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/73232; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 824-51-1 , The common heterocyclic compound, 824-51-1, name is 6-Methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H8N2, 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 solution of 6-methyl-1H-pyrrolo[2,3-b]pyri- dine (500 mg) in dichioroethane (6 mE) were added aluminum chloride (1.09 g) and acetyl chloride (0.40 mE), and then the mixture was stirred at room temperature for 1 .5 hours. The reaction solution was poured into aqueous saturated sodium hydrogen carbonate solution, and extracted with chloroform. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was triturated with isopropyl ether to give 1 -(6-methyl-1H-pyrrolo[2,3-b]pyri- din-3-yl)ethanone [REx(8-i)] (481 mg) as a yellow powder. APCI-MS mlz: 175 [M+H].

The synthetic route of 824-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceuticals Holding CO., LTD.; MITSUBISHI TANABE PHARMA CORPORATION; Iijima, Toru; Takahashi, Yoichi; Hirai, Miki; Sugama, Hiroshi; Togashi, Yuko; Shen, Jingkang; Xia, Guangxin; Wan, Huixin; US2015/232459; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 108118-69-0, 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. 108118-69-0, name is 2,6-Difluoropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 4-(tert~butoxycarbonyl-methyl-amino)-benzoic acid (70 mg, 0.28 mmol) in CHiCi2 (2 mL) was added l-chloro-N,N-2-trimethylpropenylamine (98 muL, 0.74 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (2 mL) before 2,6~difluoro-rhoyridin-3-ylamine (30 mg, 0.23 mmol) was added in one portion. After an additional 30 minutes the reaction mixture was concentrated to dryness affording a residue to which was added DMF (2 mL) and K2CO3 (64 mg, 0.46 mmol). The resulting mixture was heated by microwave to 150 0C for 10 min, after which the resulting mixture was filtered, concentrated and purified by silica gel flash chromatography (0 to 100% EtOAc in hexanes) to afford [4-(5-fluoro-oxazolo[5s4-6]pyridine-2- yl)-phenyl]-methyl-amine (50 mg, 0.21 mmol, 89%). ES MS (M+H+) – 244; Eta NMR (300 MHz, DMSO-d6): delta 8.24 (t, J – 7.7 Hz, 1 H); 7.89 (d, J = 8.4 Hz, 2 H); 7.18 (d, J = 8.4 Hz, 1 H); 6.68 (d, J = 8.5 Hz, 3 H); 2.76 (s, 3 H); HRMS m/z 244.0883 (C13H10FN3O + H+ requires 244.0881).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,108118-69-0, 2,6-Difluoropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/155017; (2009); A2;,
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. 52605-96-6, name is 2-Chloro-3-methoxypyridine, the common compound, a new synthetic route is introduced below. Product Details of 52605-96-6

The 2-chloro-3-methoxypyridine (2) (13 g, 90.6 mmol), from Step I, was stirred with 3-equivalents of sodium methoxide (14.7 g, 271.8 mmol) in dimethylformamide (100 mL) at 100 C. until completion of the reaction. The reaction mixture was then quenched with water and extracted with dichloromethane. The combined extracts were washed with water, concentrated and distilled (74 C.; 5 mm Hg) to give the product, 2,3-dimethoxypyridine (3), as a clear oil (7 g; 29% yield for two steps).1H NMR (300 MHz, CDCl3) delta 7.65 (dd, 1 H, J1=5.1 Hz, J2=1.5 Hz), 6.96(dd, 1 H, J1=7.5 Hz, J2=1.5 Hz), 6.76(dd, 1 H, J1=5.1 Hz, J2=7.7 Hz), 3.95 (s, 3 H), 3.80 (s, 3 H).

The synthetic route of 52605-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BioNumerik Pharmaceuticals, Inc.; US2008/261919; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884494-35-3 ,Some common heterocyclic compound, 884494-35-3, molecular formula is C5H3ClFNO, 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.

tert-butyl 4-(2-chloroacetamido)piperidine-1-carboxylate (2.02 g, 7.3120 mmol) and 2-chloro-5-fluoropyridin-3-ol (1.08 g, 7.32 mmol) weredissolved in DMF (70 ml). Caesium carbonate (4.88 g, 15 mmol) was added and the mixture heated to 1 oooc for 18 hours. After cooling toroom temperature the mixture was partitioned between ethyl acetateand water and the organic phase washed with water. The organic layerwas then evaporated onto silica and purified by flash column5 chromatography eluting with 20 to 100% ethyl acetate/iso-hexane togive the title compound (2.19 g, 85% yield). 1H NMR (400 MHz, CDCb):o 7.80 (d, J=2.5 Hz, 1 H), 7.23 (dd, J=2.7, 9.0 Hz, 1 H), 4.70 (s, 2H), 4.43- 4.29 (m, 3H), 2.81 (m, 2H), 2.50 – 2.37 (m, 2H), 1.74 (dd, J=1.5, 11.6Hz, 2H), 1.50 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-35-3, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; MAGARO’, Gabriele; GAROFALO, Barbara; FURLOTTI, Guido; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; (182 pag.)WO2017/211759; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13466-35-8, 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.13466-35-8, name is 3-Chloro-2-hydroxypyridine, molecular formula is C5H4ClNO, molecular weight is 129.54, as common compound, the synthetic route is as follows.

EXAMPLE 1 3-Chloro-5-octyl-2-(4-octyloxyphenyl)pyridine 10.5 ml (203.0 mmol) of bromine are added dropwise at 0 C. to 23.9 g (184.5 mmol) of 3-chloro-2-hydroxypyridine in 240 ml of dimethylformamide, and the mixture is stirred at room temperature for 2 hours. 200 ml of water are subsequently added, and 30 g of sodium sulfite in 100 ml of water are added dropwise. After 15 minutes, the mixture is extracted three times with 200 ml of dichloromethane in each case, the combined organic phases are dried over sodium sulfate and filtered, and the filtrate is evaporated to dryness, giving 36.58 g of 5-bromo-3-chloro-2-hydroxypyridine. STR13 m.p.: 168 C. (decomp.)

The chemical industry reduces the impact on the environment during synthesis 13466-35-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoechst Aktiengesellschaft; US5629428; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64951-08-2, 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 64951-08-2 as follows.

Step (d) N-[4-(l-cyclopentyl-6-fluoro-2,4-dioxo-l,4-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)cyclohexyl]imidazo[l,2-a]pyridine-2-carboxamide To a mixture of imidazo[l,2-a]pyridine-2-carboxylic acid (89mg, 0.55mmol), HATU(220mg, 0.55mmol), HOAT (75mg, 0.55mmol) and 3-(4-aminocyclohexyl)-l-cyclopentyl-6-fluoro-pyrido[2,3-d]pyrimidine-2,4(lH,3H)-dione hydrochloride (176mg, 0.46mmol) inN-methylpyrrolidinone (10ml) was added ethyl-di-isopropylamine (0.31ml, 1.81mmol) over a period of 20 seconds. Stirring was continued at ambient temperature for 3 days and the reaction mixture was poured onto water. The obtained solid was filtered, dried on the sinter, dissolved in chloroform and adsorbed onto silica gel. Flash chromatography using a mixture of petrol ether and ethyl acetate yielded the title compound (55mg, 24%) as a colourless solid.1H NMR (300MHz, DMSO-J*): delta 8.77 (IH, d); 8.60 (IH, ddd); 8.40 (IH, s); 8.25 (IH, dd); 7.78 (IH, d); 7.68 (IH, d); 7.38 (IH, dd); 7.00 (IH, dd); 5.80 (IH, p); 4.84 (IH, bt);2.89 (IH, bs); 2.50 – 2.70 (2H, bm); 2.04 – 2.22 (2H, bd); 1.41 – 2.04 (12H, m).APCI-MS m/z: 491 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64951-08-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84223; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem