Tag: M.W:100-200

Synthetic Route of 847729-27-5, 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.847729-27-5, name is Methyl 2-chloro-5-fluoronicotinate, molecular formula is C7H5ClFNO2, molecular weight is 189.57, as common compound, the synthetic route is as follows.

STEP 2. Methyl 5-fluoro-2- (4-fluorobenzvl) nicotinate; To a stirred solution of methyl 2-chloro-5-fluoronicotinate (step 1, 350 mg, 1.85 mmol) and dichlorobis [triphenylphosphine] nickel (1I) (362 mg, 0.55 mmol) in tetrahydrofuran (15 mL) was added a 0.5 M solution of 4-fluorobenzylzinc chloride in tetrahydrofuran (5.54 mL, 2.77 mmol) at 0 C under nitrogen. The resulting mixture was warmed to room temperature and stirred for 16 h. The mixture was poured into saturated aqueous ammonium chloride solution (50 mL) and extracted with ethyl acetate (100 ML). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (10/1) to afford 439 mg (90%) of the title compounds as colorless oil: H-NMR (CDC13) 6 8.56 (1H, d, J = 2.8 Hz), 7.91 (1H, dd, J = 8.6, 2.9 Hz), 7.26-7. 19 (2H, m), 6.98-6. 92 (2H, M), 4.52 (2H, s), 3.89 (3H, s); MS (ESI) m/z 264 (M + H) +.

Statistics shows that 847729-27-5 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-5-fluoronicotinate.

Reference:
Patent; PFIZER INC.; PFIZER JAPAN, INC.; WO2005/21508; (2005); 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 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-(Trifluoromethyl)pyridin-3-amine

5-(Trifluoromethyl)pyridin-3 -amine (977 mg, 6.03 mmol, Anichem, P20551 , North Brunswick, NJ) was treated with THF (40 mL) and LiHMDS (1.0 M in THF, 13.26 mL, 13.26 mmol) slowly dropwise at RT and stirred at this temperature for 20 min. The solution was then cooled in an ice bath and di-tert-butyl dicarbonate (1.38 g, 6.33 mmol) was added and the solution stirred warming to RT overnight. LC-MS indicated partial conversion to bis(Boc) material (M+l =363.2). The reaction mixture was treated with additional di-tert-butyl dicarbonate (1.38 g, 6.33 mmol) and of 1M LiHMDS and stirred overnight (16 h). The reaction mixture was concentrated and the crude material was treated with 0.2M HC1 (aq., 30 mL) and extracted with EtOAc (100 mL). The organic layer was washed with a saturated solution of NaHCC>3 (aq.) and brine and dried over MgS04, filtered and concentrated. The resulting crude product was purified by silica gel chromatography (20-50% EtOAc in hexanes) to afford bis(teri-butyl (5- (trifluoromethyl)pyridin-3-yl)carbamate) (729 mg, 33 % yield) as a yellow crystalline solid. MS (ESI, pos. ion) m/z: 363.0 (M+l). .H NMR (400 MHz, CDCl3) delta ppm 8.80 (1 H, s), 8.58 – 8.64 (1 H, m), 7.75 (1 H, s), 1.44 (18 H, s). 19F NMR (377 MHz, CDCl3) delta ppm -62.36 (3 F, s).

With the rapid development of chemical substances, we look forward to future research findings about 112110-07-3.

Reference:
Patent; AMGEN INC.; D’AMICO, Derin C.; HERBERICH, Bradley J.; JACKSON, Claire L.M.; PETTUS, Liping H.; TASKER, Andrew; WANG, Hui-Ling; WU, Bin; WURZ, Ryan; WO2012/148775; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1132-37-2, 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. 1132-37-2, name is Dipyridin-2-ylmethane, molecular formula is C11H10N2, 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.

100cc Schlenk tube and then in the oxygen and three times replacement with argon and vacuum for removal of water Pt[2,2′-bpyridine]Cl2 (90.34mg, 0.214mmol) was added and dissolved with EtOH solvent (20ml). To this solution was added dipyridin-2-ylmethane (40mg, 0.235mmol) was dissolved in EtOH (15ml). The mixture is contained in a Schlenk tube for 5 hours and then put Reflux NH4PF6 (114.9mg, 0.705mmol) was refluxed with 80C for 36 hours under argon gas. After confirming the completion of the reaction by TLC whether the mixture was cooled at room temperature. Conducted a filter to remove the resulting precipitate was cooled, and the supernatant was filtered through a filter and then dried in vacuum and then washed CHCl3 to give the title compound (yield: 57%).

According to the analysis of related databases, 1132-37-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sunchon National University Industry-Academic Cooperation Foundation; Jung, Min Chul; Kim, Song Chan; (13 pag.)KR101602456; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3430-22-6, 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 3430-22-6, name is 3-Bromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3.98 g of the acid obtained in the previous step (20 mmol, 1 eq.) in 50 ml of methanol is reflux heated in the presence of 4 ml of concentrated sulfuric acid. The mixture is allowed to return to ambient temperature and extracted 3 times with ethyl acetate. The organic phase is dried on Na2SO4 and the solvent is evaporated. 2.65 g (62%) of esterified product is obtained. NMR (1H, CDCl3): 4.02 (s; 3H), 7.64 (d, J=4.9 Hz; 1H), 8.63 (d, J=4.9 Hz; 1H), 8.88 (s; 1H).

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 3430-22-6, 3-Bromo-4-methylpyridine.

Reference:
Patent; Imbert, Thierry; Monse, Barbara; Koek, Wouter; US2005/80085; (2005); 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 6515-09-9, name is 2,3,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H2Cl3N

Saponification: 100 g of 2,3,6-trichloropyridine, 76 g of sodium hydroxide,450g of water reacts in an autoclave at 130C for about 6 hours.Slowly to normal temperature,filter,The filter cake is washed thoroughly with water,Wash water is used for application.The filter cake was obtained 3,6-dichloro-pyridinol sodium sulfate to give 70g.

With the rapid development of chemical substances, we look forward to future research findings about 6515-09-9.

Reference:
Patent; Suzhou Kaiyuan People’s Welfare Technology Co., Ltd.; Zhao Fei; Song Liang; Chen Wei; Wei Haihao; Zeng Miao; Xu Jianfeng; (8 pag.)CN107935921; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 52605-96-6, name is 2-Chloro-3-methoxypyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-3-methoxypyridine

To a solution of Compound 8 (68 mg) in 2-propanol (5 ml) were added 2-chloro-3-methoxy pyridine (87 mg) and concentrated sulfuric acid (90 mg). It was stirred under reflux for 40 hours. Saturated sodium bicarbonate solution and water were added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. The obtained residue was purified by column chromatography. The obtained solid was recrystallized with diethylether-hexane to give Compound 1-6 (25 mg).1H-NMR (CDCl3) delta: 1.58 (3H, s), 2.02-2.12 (1H, m), 2.33-2.42 (1H, m), 3.82-4.00 (3H, m), 3.89 (3H, s), 4.09-4.17 (1H, m), 6.67 (1H, dd, J=7.9, 5.0 Hz), 6.93-6.99 (2H, m), 7.01 (1H, brs), 7.34 (1H, dd, J=7.9, 3.0 Hz), 7.79 (1H, dd, J=5.0, 1.3 Hz), 8.02-8.08 (1H, m)

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, 52605-96-6, 2-Chloro-3-methoxypyridine.

Reference:
Patent; SHIONOGI & CO., LTD.; US2012/238557; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83766-88-5, 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. 83766-88-5, name is 2-(tert-Butoxy)pyridine. A new synthetic method of this compound is introduced below.

General procedure: Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83766-88-5, its application will become more common.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 134363-45-4, 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. 134363-45-4, name is 2-(Pyridin-3-yl)benzoic acid, molecular formula is C12H9NO2, 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.

A 250 ml_, round-bottomed flask under a positive pressure of nitrogen was equipped with a magnetic stirrer and charged with anhydrous DMF (70 ml_) followed by 2-[4-(4-amino-2-fluoro-phenyl)-piperazin-1 -yl]-N,N-diethyl-2- phenyl-acetamide (3.5 g, 9.1 mmol), 2-pyhdin-3-yl-benzoic acid (1.9 g, 9.5 mmol), HATU (3.8 g, 10.0 mmol) and DIPEA (1.3 g, 10.0 mmol). The resulting brown colored reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was then concentrated on the rotary evaporator to yield an oil. To this oil was added, dichloromethane (100 ml_) and 1 N NaOH (50 ml_). The biphasic solution was stirred for 0.5 h after which phases were separated. The aqueous layer was extracted with dichloromethane (2 X 25 ml_). The organic layers were pooled, dried over anhydrous sodium sulfate, filtered and concentrated to yield a viscous brown oil. The oil was taken in ethanol (100 ml_) and heated to -6O0C in a water bath for 1 h. The resulting mixture was diluted with MTBE (added with magnetic stirring in 25 ml_ portions, total 125 ml_). The resulting suspension was stirred at O0C (ice/water bath) for 2 h. The product was collected by filtration through a medium porosity glass frit, washed with a mixture of EtOH/MTBE (1 :1.25, 22.5 ml_ X 2) and the filter- cake dried thoroughly under house vacuum to yield the title compound as an off-white solid.MS (ESI): mass calcd. for C34H36FN5O2, 565.29; m/z found, 566.4 [M+H]+.1H-NMR(400 MHz, DMSO-d6) delta ppm: 10.65 (s, 1 H), 10.5 (bs, 1 H), 8.92 (s, 1 H), 8.82 (d, J = 5.5 Hz, 1 H), 8.39 (d, J = 7.6 Hz, 1 H), 7.96 (dd, J = 7.8, 5.6 Hz, 1 H), 7.76 (d, J = 7.6 Hz, 1 H), 7.70-7.63 (m, 4H), 7.56-7.50 (m, 4H), 7.26 (dd, J = 8.7, 1.7 Hz, 1 H), 7.02 (t, J = 9.4 Hz, 1 H), 5.97 (s, 1 H), 3.63-3.61 (m, 1 H), 3.48-3.15 (m, 10H), 2.67-2.65 (m, 1 H), 1.10-1.01 (m, 3H), 0.82-0.80 (m, 3H).

According to the analysis of related databases, 134363-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2009/6185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 60753-14-2 , The common heterocyclic compound, 60753-14-2, name is 4-(Pyridin-3-yl)butan-1-ol, molecular formula is C9H13NO, 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) N-(3-Nicotinylpropyl)benzylamine To a solution of 3-nicotinyl-1-propanol (50.0 g, 365 mmol) and triethylamine (110 g, 1.09 mol) in methylene chloride (500 ml) at 0 C. was added dropwise methanesulfonyl chloride (83.5 g, 7.29 mmol). The solution was stirred at 0 C. for 1 hour and then RT for 1 hour, and the excess of methanesulfonyl chloride was carefully decomposed with ice-water. The organic layer was separated and washed with water (twice). The aqueous layer and washings were combined, basified with 50% aqueous sodium hydroxide, and extracted with methylene chloride (3 times). The methylene chloride extracts were combined, washed with saturated brine solution, dried (MgSO4), and evaporated to give 72.0 g (92% yield) of the mesylate which was used immediately for the further reaction. A solution of the mesylate (72.0 g, 334 mmol) and benzylamine (179.2 g, 1.6 mol) in DMSO (300 ml) was stirred at RT overnight. The reaction mixture was poured into 2 l of water and extracted with ethyl acetate (three times). The extracts were dried with MgSO4, thus yielding 75 g of a red oil after evaporation of benzylamine. The oil was used directly for the next reaction without further purification.

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

Reference:
Patent; Fisons Corporation; US4889941; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90993-26-3, Adding some certain compound to certain chemical reactions, such as: 90993-26-3, name is 7-Bromo-1H-imidazo[4,5-c]pyridine,molecular formula is C6H4BrN3, 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 90993-26-3.

Step 3: 7-bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridine 5-oxide To a stirred solution of 7-bromo-lH-imidazo[4,5-c]pyridine 5-oxide (425 mg, 1.99 mmol) and N,N- dimethylformaldehyde (5.5 mL) at 0 C was added N,N-diisopropylethylamine (1.05 mL, 5.96 mmol), tetrabutylammonium iodide (74 mg, 0.199 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (0.78 mL, 3.97 mmol) and the reaction mixture stirred for 30 min at RT. The reaction mixture was washed with water (10 mL) and extracted with dichloromethane (2 x 10 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 10% methanol in dichloromethane) affording an approximate 3:2 mixture of 7-bromo-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridine 5-oxide and 7-bromo-3-((2- (trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine 5-oxide N-(2- (trimethylsilyl)ethoxy)methane regioisomers as an orange foam (580 mg, 54%): H NMR (400 MHz, DMSO-d6; reported as an approximate 3:2 mixture of N-(2-(trimethylsilyl)ethoxy)methane isomers) delta 8.73 (d, = 1.5 Hz, 0.6 H), 8.60 (d, = 1.6 Hz, 1H), 8.38 (d, = 1.5 Hz, 1H), 8.36 (d, = 1.5 Hz, 0.6H), 8.10 (s, 1H), 8.09 (s, 0.6H), 5.76 (s, 1.3H), 5.48 (s, 2H), 3.63 – 3.59 (m, 1.4H), 3.56 – 3.50 (m, 2H), 0.97 – 0.91 (m, 3H), -0.01 (s, 9H), -0.02 (s, 6H).

According to the analysis of related databases, 90993-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem