Tag: M.W=300-400

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. 505084-55-9, name is 2-Chloro-5-(trifluoromethyl)-4-iodopyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Example 21; 5-(2-(2-methoxy-4-morpholinophenylamino)-5-(trifluoromethyl)pyridin-4- ylamino)-N-methylthiazole-4- carboxamide; 2-chloro-5-(trifluoromethyl)pyridin-4-amine; 2-chloro-4-iodo-5-(trifluoromethyl)pyridine was dissolved in 7 M Ammonia/Methanol. It was heated in a Biotage Initiator microwave synthesizer at 130 C for 1 h. A mixture of the 2- and 4-substituted products was obtained. The solvent was removed and the residue was purified by silica gel chromatography (DCM/MeOH) gradient. The pure title compound was isolated.

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, 505084-55-9, 2-Chloro-5-(trifluoromethyl)-4-iodopyridine.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2008/115369; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, 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, 153747-97-8, blongs to pyridine-derivatives compound. Computed Properties of C14H20BrN3O2

General procedure: A reaction tube was charged with benzenesulfonyl fluorideboronic acid 3 (61 mg, 0.30 mmol, 1.5 equiv), Pd(OAc)2 (2.3 mg, 0.010 mmol, 5.0 mol %) and XPhos (9.5 mg, 0.020 mmol, 10 mol %), sealed with a rubber septum, evacuated and back-filled with N2 three times. Degassed 1,4-dioxane (0.8 mL), degassed 1.0 M aq. K3PO4 solution (0.4 mL, 0.40 mmol, 2.0 equiv) and aryl halide* (0.20 mmol, 1.0 equiv) were added subsequently, and the reaction mixture stirred under positive pressure of N2 in a preheated aluminium heating block at 40 C for 4 h (5a, b, f, g, h, l), 6 h (5c, d, e, i, j, m) or 24 h (5k). After cooling to ambient temperature, the reaction mixture was diluted with EtOAc, dried with anhydrous MgSO4, filtered over Celite and concentrated in vacuo. The crude product was purified by flash column chromatography to afford the biarylsulfonyl fluoride. *In the case where aryl halide is a solid, it was added to the vessel before evacuating and back-filling.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Article; Lou, Terry Shing-Bong; Willis, Michael C.; Tetrahedron; vol. 76; 1; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 915720-71-7, 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.915720-71-7, name is (S)-tert-Butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate, molecular formula is C12H17BrN2O2, molecular weight is 301.18, as common compound, the synthetic route is as follows.

To a stirred solution OfZnBr2 (7.85 g, 34.9 mmol) in THF (40 ml) was added cyclopropylmagnesium bromide (54.8 ml, 27.4 mmol) in THF dropwise at -78 0C. After stirring at -78 0C for 30 minutes, the resulting solution was warmed to 0 0C and stirred at EPO 0 C for 30 minutes. (S)-tert-Butyl-l-(5-biOmopyridin-2-yl)ethylcarbamate (Method 27; 3.00 g, 9.96 mmol) and Pd(PPh3)4 (0.576 g, 0.498 mmol) were added successively. The resulting mixture was stirred at 60 0C for 3 hours. After cooled to room temperature, 100 ml of saturated ammonium chloride was added, extracted with EtOAc and dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography (hexane-EtOAc = 4:1) to give the title compound as a white solid (2.04 g, 78%). 1H NMR (400 MHz) delta 8.30 (d, J= 2.0 Hz, IH), 7.37 (dd, J= 1.6 and 8.0 Hz, IH), 7.25 (d, J= 7.6 Hz , IH), 7.20 (d, J= 8.4 Hz, IH)5 4.61 (m, IH), 1.92 (m, IH), 1.37 (s, 9H), 1.29 (d, J= 12 Hz, 3H), 0.96 (m, 2H), 0.69 (m, 2H). MS: Calcd.: 262; Found: [M+H]+263.

The chemical industry reduces the impact on the environment during synthesis 915720-71-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/123113; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 123853-39-4, 4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic 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, 123853-39-4, blongs to pyridine-derivatives compound. Product Details of 123853-39-4

The 75mg about 0.21mmol prepared above S14,80mg, about 0.21mmol compound S12,55mg about 0.4mmol K2CO3 in single-neck flask, 5mL DMF, in a nitrogen atmosphere Heated to 50 C, the reaction 2h, cooled to 30 C overnight reaction, until the reaction is complete, add 20mL Water was added and extracted with chloroform, the organic phases were pooled washed with water and saturated brine, dried over anhydrous sodium sulfate Dry, filtered, and solvent was removed by rotary evaporation, the residue was purified by column chromatography to give the present invention provides Compound 9,46mg, a yield of 35%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,123853-39-4, its application will become more common.

Reference:
Patent; JiangsuSimcere Pharmaceutical Company, Ltd; JiangsuSimcere Pharmaceutical Research Co. Ltd.; Chen, Rong; Liu, Fei; Cong, Xin; Feng, Lin; Li, Haidao; Dong, Qingli; (62 pag.)CN102464608; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 848500-12-9 ,Some common heterocyclic compound, 848500-12-9, molecular formula is C15H22BrN3O2, 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.

Step 6: tert-butyl 1-(6-(2-(benzyloxy)-1 , 1,3,3-tetramethyl-2,3-dihydro- 1H-inden-5- yl)pyridin-2-yl)piperidin-4-ylcarbamate:Nitrogen was bubbled through a solution of 2-(2-(benzyloxy)-1 ,1 ,3,3-tetramethyl-2,3- dihydro-1 H-inden-5-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (0.148 g, 0.365 mmol) , tert-butyl 1 -(6-bromopyridin-2-yl)piperidin-4-ylcarbamate (0.100 g, 0.281 mmol)PdCI2(dppf) CH2CI2 (0.018 g, 0.022 mmol) and 2N aqueous sodium carbonate (0.291 mL, 0.561 mmol) in dioxane (1 .2 ml) for 10 min and subsequently heated at 90 °C for 15h. After cooling to room temperature, the reaction mixture was diluted with DCM/water and filtered through a phase separator cartridge. The filtrate was concentrated in vacuo and the residue purified by flash chromatography using a Biotage SP4 instrument to afford the title compound (0.039 g, 25percent).LCMS (Method F): RT = 2.06 min, M+H+ = 350; 1H NMR (500 MHz, CDCI3): 7.84 (d, 1 H), 7.70 (s, 1 H), 7.50 (t, 1 H), 7.40 (2, 2H), 7.38 (d, 2H), 7.30 (t, 1 H), 7.19 (d, 1 H), 7.05 (d, 1 H), 6.58 (d, 1 H), 4.80 (s, 2H), 4.49 (brs, 1 H), 4.31 (m, 2H), 3.71 (m, 2H), 3.02 (m, 2H), 2.02 (m, 2H), 1 .70 (m, 1 H), 1 .45 (s, 9H), 1 .39 (s, 3H), 1 .29 (s, 3H), 1 .27 (s, 3H).

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. 848500-12-9, tert-Butyl (1-(6-bromopyridin-2-yl)piperidin-4-yl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMAC DISCOVERY LIMITED; HARRISON, Timothy; BURKAMP, Frank; JORDAN, Linda; BELL, Mark; JANSSEN, Dominic; MIEL, Hugues; MCFARLAND, Mary; WO2012/69852; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 16727-47-2, 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 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

Preparation of 25-2 To a stirred solution of 24-2 (455mg, 1.22 mmol) in toluene was added 25-1 (100 mg, 860.86 mumol) and K3PO4.H2O (494 mg, 215 mumol) and the resulting mixture was degassed with Argon for 10 minutes. To this were added CuI (0.05 mg, 0.26 mumol) and trans-N,N?- dimethylcyclohexane-1,2-diamine (17 mg, 120 mumol) and heated to 100C for 16 hours to produce 25-2. Reaction mixture was cooled to room temperature and filtered through a short bed of celite. The filtrate was diluted with Ethyl acetate, washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Crude mass was purified doing column chromatography (silica, gradient: 0-20% Ethyl acetate in Hexane) to afford 25-2 (200 mg, 514 mumol, 60%) as sticky off-white solid. LC MS: ES+ 390.2.

According to the analysis of related databases, 16727-47-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; CHEN, Chi-li; DUPLESSIS, Martin; HE, Minsheng; LAZARSKI, Kiel; (980 pag.)WO2017/197051; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 193274-02-1 , The common heterocyclic compound, 193274-02-1, name is tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate, molecular formula is C19H25N3O3, 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.

Step D. 3a(R)-Benzyl-2-methyl-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one (L)-tartrate To a 2 liter, round bottom flask, equipped with a mechanical stirrer, addition funnel, and a thermocouple was added, sequentially, 3a-(R,S)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]-pyridine-5-carboxylic acid tert-butyl ester (prepared according to Step C, 51.5 g, 0.15 moles, 1.0 equivalents) and methylene chloride (515 ml, 10 volumes). The mixture was agitated to form a solution which was then cooled to an internal temperature of 0 C.-5 C. To the cooled mixture was added trifluoroacetic acid (TFA, 130 ml, 192 g, 1.68 moles, 11.2 eq., 2.5 volumes). The TFA was added via the addition funnel over 15 minutes while maintaining an internal temperature of 0 C.-5 C. The reaction mixture was warmed to about 20 C. over 3 hours and then the reaction mixture was cooled to 10 C.-15 C. To the cooled reaction mixture was added sodium carbonate (92 g, 0.868 moles) in water (920 mL) over 20 minutes. The pH was 7.5. The reaction mixture was transferred to a 2 liter separatory funnel and allowed to settle. The organic portion was decanted and the aqueous portion was extracted with methylene chloride (130 ml, 2.5 volumes). The combined organic portions were transferred back to the 2 liter reactor and to it was added L-tartaric acid (24.77 g, 0.165 moles, 1.1 equivalents) dissolved in acetone (354 ml, about 7 volumes) and water (44 mL, about 1 volume). The reaction mixture was agitated and heated at about 38 C. overnight. The resultant slurry was cooled to 0 C.-5 C., granulated for 1 hour, then filtered. The solids were washed with 100 ml of cold acetone and then dried in vacuo at 40 C.-50 C. for 16 hours to afford 51.86 g (87.9% yield) of the title compound of Step D.

The synthetic route of 193274-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Busch, Frank R; Chiu, Charles K; Meltz, Clifford N; Post, Ronald J; Rose, Peter R; US2002/2283; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 79491-46-6, 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. 79491-46-6, name is 2,6-Dibromo-3-methoxy-5-nitropyridine, molecular formula is C6H4Br2N2O3, 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.

5.43 3-Methoxy-5-nitropyridine-2,6-diamine (33) A solution of 32 (0.5 g, 1.6 mmol) in aqueous ammonia (15 M, 12 mL, 180 mmol) was heated at 90 C for 1 h in a microwave oven. The reaction mixture was cooled, the yellow solid was collected by filtration, washed with a small amount of water, and dried under vacuum to afford 33 (230 mg, 78%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6, 393 K) delta = 7.48 (s, 1H), 7.35 (br, 2H), 6.81 (br, 2H), 3.80 (s, 3H); MS ES+ve m/z 185 (M+H)+.

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 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine.

Reference:
Article; Miah, Afjal H.; Abas, Hossay; Begg, Malcolm; Marsh, Benjamin J.; O’Flynn, Daniel E.; Ford, Alison J.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Steve A.; Rumley, Sally-Anne; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4298 – 4311;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16727-47-2, 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.16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, molecular weight is 370.2398, as common compound, the synthetic route is as follows.

To the stirred solution of (2,6-dibenzyloxy-3-bromo-pyridine) 43-1 (5 g, 13.50 mmol)in dry THF (30 mL), 2.5 M BuLi in Hexane (7.08 g, 20.26 mmol) was added at -78C under inertatmosphere and stirred for 1 hour at rt. After that, dry DMF (1.5 mL) was added to the reactionmixture dropwise at -78C and stirring was continued for further 2 hours at room temperature. After completion of reaction, as evidenced from TLC, reaction mixture was quenched withsaturated ammonium chloride solution. The aqueous phase was extracted with ethyl acetate.Combined organic layer was separated, dried over anhydrous sodium sulfate and concentratedunder vacuum. The crude reaction mass was purified by column chromatography to obtain5 desired compound 43-2 (2,6-dibenzyloxypyridine-3-carbaldehyde) (2.8 g, 8.77 mmol, 64.92%yield) as sticky solid. ES (M+H): 320.

Statistics shows that 16727-47-2 is playing an increasingly important role. we look forward to future research findings about 2,6-Bis(benzyloxy)-3-bromopyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Christoper, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; DUPLESSIS, Martin; CHEN, Chi-Li; (791 pag.)WO2018/237026; (2018); 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. 53710-18-2, name is 3,5-Diiodopyridine, molecular formula is C5H3I2N, 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. Recommanded Product: 3,5-Diiodopyridine

In a 75-mL sealed tube, 3,5-diiodo-pyridine (intermediate A-5, 6.6 g, 20 mmol), 5-chloro- 3,3-dimethyl-2,3-dihydro-isoindol-1-one (intermediate A-3, 1.95 g, 10 mmol), CuT (571 mg, 3 mmol), K3P04 (4.24 g, 20 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.7 mL, 6 mmol) were dissolved in 20 mL of dioxane. The resulting reaction mixture was heated at120C for 3 hours before it was poured into water (50 mL) and extracted with EtOAc (2 x125 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by silica gel flash chromatography (0-30% EtOAc-hexane gradient) to yield the title compound (1.8 g, 45%) as a light yellow solid. MS: 399.2 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 53710-18-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191338; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem